Heterocyclic compound and organic light emitting device comprising same

ABSTRACT

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device including the same.

TECHNICAL FIELD

The present specification relates to a heterocyclic compound, and anorganic light emitting device including the same.

The present specification claims priority to and the benefits of KoreanPatent Application No. 10-2019-0088238, filed with the KoreanIntellectual Property Office on Jul. 22, 2019, the entire contents ofwhich are incorporated herein by reference.

BACKGROUND ART

An electroluminescent device is one type of self-emissive displaydevices, and has an advantage of having a wide viewing angle, and a highresponse speed as well as having an excellent contrast.

An organic light emitting device has a structure disposing an organicthin film between two electrodes. When a voltage is applied to anorganic light emitting device having such a structure, electrons andholes injected from the two electrodes bind and pair in the organic thinfilm, and light emits as these annihilate. The organic thin film may beformed in a single layer or a multilayer as necessary.

A material of the organic thin film may have a light emitting functionas necessary. For example, as a material of the organic thin film,compounds capable of forming a light emitting layer themselves alone maybe used, or compounds capable of performing a role of a host or a dopantof a host-dopant-based light emitting layer may also be used. Inaddition thereto, compounds capable of performing roles of holeinjection, hole transfer, electron blocking, hole blocking, electrontransfer, electron injection and the like may also be used as a materialof the organic thin film.

Development of an organic thin film material has been continuouslyrequired for enhancing performance, lifetime or efficiency of an organiclight emitting device.

DISCLOSURE Technical Problem

The present specification is directed to providing a heterocycliccompound, and an organic light emitting device including the same.

Technical Solution

One embodiment of the present specification provides a heterocycliccompound represented by the following Chemical Formula 1.

In Chemical Formula 1,

X is O or S,

L is a direct bond; a substituted or unsubstituted C6 to C60 arylenegroup; or a substituted or unsubstituted C2 to C60 heteroarylene group,

Z and R1 are each independently a substituted or unsubstituted C1 to C60alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; asubstituted or unsubstituted C2 to C60 alkynyl group; a substituted orunsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstitutedC2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 toC60 aryl group; a substituted or unsubstituted C2 to C60 heteroarylgroup; a substituted or unsubstituted C1 to C20 alkylamine group; asubstituted or unsubstituted C6 to C60 arylamine group; a substituted orunsubstituted C2 to C60 heteroarylamine group; or a substituted orunsubstituted phosphine oxide group,

R2 to R7 are each independently hydrogen; deuterium; a halogen group; acyano group; a substituted or unsubstituted C1 to C60 alkyl group; asubstituted or unsubstituted C3 to C60 cycloalkyl group; a substitutedor unsubstituted C6 to C60 aryl group; or a substituted or unsubstitutedC2 to C60 heteroaryl group,

a is 1 or 2,

b is an integer of 1 to 3,

m and n are each an integer of 1 to 5, and

when a, b, m and n are each 2 or greater, substituents in theparentheses are the same as or different from each other.

Another embodiment of the present application provides an organic lightemitting device including a first electrode; a second electrode providedopposite to the first electrode; and an organic material layer providedbetween the first electrode and the second electrode, wherein theorganic material layer includes the heterocyclic compound represented byChemical Formula 1.

Another embodiment of the present application provides an organic lightemitting device including a first electrode; a first stack provided onthe first electrode and including a first light emitting layer; a chargegeneration layer provided on the first stack; a second stack provided onthe charge generation layer and including a second light emitting layer;and a second electrode provided on the second stack, wherein the chargegeneration layer includes the heterocyclic compound represented byChemical Formula 1.

Advantageous Effects

A compound described in the present specification can be used as amaterial of an organic material layer of an organic light emittingdevice. In the organic light emitting device, the compound is capable ofperforming a role of a hole injection material, a hole transfermaterial, a light emitting material, an electron transfer material, anelectron injection material or the like. Particularly, the compound canbe used as an electron transfer layer material or a charge generationlayer material of an organic light emitting device.

Particularly, Chemical Formula 1 has a structure in which dibenzofuranor dibenzothiophene is fused to quinoline, and HOMO and LUMO levels canbe adjusted by having various substituents in the benzene ring which isnot fused to the quinoline in the dibenzofuran or dibenzothiophene.Accordingly, electrical properties of the structure can be enhanced byadjusting an energy band gap. In addition, electron transfer capabilityof a material can be enhanced through substituents having strongelectron migration properties.

Specifically, when using the compound represented by Chemical Formula 1in an organic material layer, a driving voltage of the device can belowered, light efficiency can be enhanced, and lifetime properties ofthe device can be enhanced.

DESCRIPTION OF DRAWINGS

FIG. 1 to FIG. 4 each illustrate a lamination structure of an organiclight emitting device according to one embodiment of the presentspecification.

-   -   100: Substrate    -   200: Anode    -   300: Organic Material Layer    -   301: Hole Injection Layer    -   302: Hole Transfer Layer    -   303: Light Emitting Layer    -   304: Electron Transfer Layer    -   305: Electron Injection Layer    -   400: Cathode

MODE FOR DISCLOSURE

Hereinafter, the present specification will be described in more detail.

In the present specification, a certain part “including” certainconstituents means capable of further including other constituents, anddoes not exclude other constituents unless particularly stated on thecontrary.

In the present specification, the term “substitution” means a hydrogenatom bonding to a carbon atom of a compound being changed to anothersubstituent, and the position of substitution is not limited as long asit is a position at which the hydrogen atom is substituted, that is, aposition at which a substituent can substitute, and when two or moresubstituents substitute, the two or more substituents may be the same asor different from each other.

In the present specification, a “T1 value” means an energy level valuein a triplet state.

In the present specification, “substituted or unsubstituted” means beingsubstituted with one or more substituents selected from the groupconsisting of a halogen group; a cyano group; a C1 to C60 linear orbranched alkyl group; a C2 to C60 linear or branched alkenyl group; a C2to C60 linear or branched alkynyl group; a C3 to C60 monocyclic orpolycyclic cycloalkyl group; a C2 to C60 monocyclic or polycyclicheterocycloalkyl group; a C6 to C60 monocyclic or polycyclic aryl group;a C2 to C60 monocyclic or polycyclic heteroaryl group; a silyl group; aphosphine oxide group; and an amine group, or being unsubstituted, orbeing substituted with a substituent linking two or more substituentsselected from among the substituents illustrated above, or beingunsubstituted.

In the present specification, the halogen may be fluorine, chlorine,bromine or iodine.

In the present specification, the alkyl group includes linear orbranched having 1 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkyl groupmay be from 1 to 60, specifically from 1 to 40 and more specificallyfrom 1 to 20. Specific examples thereof may include a methyl group, anethyl group, a propyl group, an n-propyl group, an isopropyl group, abutyl group, an n-butyl group, an isobutyl group, a tert-butyl group, asec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentylgroup, an n-pentyl group, an isopentyl group, a neopentyl group, atert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentylgroup, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, ann-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, acyclohexylmethyl group, an octyl group, an n-octyl group, a tert-octylgroup, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentylgroup, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propylgroup, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentylgroup, a 4-methylhexyl group, a 5-methylhexyl group and the like, butare not limited thereto.

In the present specification, the alkenyl group includes linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkenyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20. Specific examples thereof may include a vinyl group, a1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, anallyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-ylgroup, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, astyrenyl group and the like, but are not limited thereto.

In the present specification, the alkynyl group includes linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkynyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20.

In the present specification, the cycloalkyl group includes monocyclicor polycyclic having 3 to 60 carbon atoms, and may be furthersubstituted with other substituents. Herein, the polycyclic means agroup in which the cycloalkyl group is directly linked to or fused withother cyclic groups. Herein, the other cyclic groups may be a cycloalkylgroup, but may also be different types of cyclic groups such as aheterocycloalkyl group, an aryl group and a heteroaryl group. The numberof carbon groups of the cycloalkyl group may be from 3 to 60,specifically from 3 to 40 and more specifically from 5 to 20. Specificexamples thereof may include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a 3-methylcyclopentyl group, a2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexylgroup, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, acycloheptyl group, a cyclooctyl group and the like, but are not limitedthereto.

In the present specification, the heterocycloalkyl group includes O, S,Se, N or Si as a heteroatom, includes monocyclic or polycyclic having 2to 60 carbon atoms, and may be further substituted with othersubstituents. Herein, the polycyclic means a group in which theheterocycloalkyl group is directly linked to or fused with other cyclicgroups. Herein, the other cyclic groups may be a heterocycloalkyl group,but may also be different types of cyclic groups such as a cycloalkylgroup, an aryl group and a heteroaryl group. The number of carbon atomsof the heterocycloalkyl group may be from 2 to 60, specifically from 2to 40 and more specifically from 3 to 20.

In the present specification, the aryl group includes monocyclic orpolycyclic having 6 to 60 carbon atoms, and may be further substitutedwith other substituents. Herein, the polycyclic means a group in whichthe aryl group is directly linked to or fused with other cyclic groups.Herein, the other cyclic groups may be an aryl group, but may also bedifferent types of cyclic groups such as a cycloalkyl group, aheterocycloalkyl group and a heteroaryl group. The aryl group includes aspiro group. The number of carbon atoms of the aryl group may be from 6to 60, specifically from 6 to 40 and more specifically from 6 to 25.Specific examples of the aryl group may include a phenyl group, abiphenyl group, a triphenyl group, a naphthyl group, an anthryl group, achrysenyl group, a phenanthrenyl group, a perylenyl group, afluoranthenyl group, a triphenylenyl group, a phenalenyl group, apyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenylgroup, an indenyl group, an acenaphthylenyl group, a benzofluorenylgroup, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a fusedring thereof, and the like, but are not limited thereto.

In the present specification, the silyl group is a substituent includingSi, having the Si atom directly linked as a radical, and is representedby —SiR₁₀₄R₁₀₅R₁₀₆. R₁₀₄ to R₁₀₆ are the same as or different from eachother, and may be each independently a substituent formed with at leastone of hydrogen; deuterium; a halogen group; an alkyl group; an alkenylgroup; a cycloalkyl group; an aryl group; and a heterocyclic group.Specific examples of the silyl group may include a trimethylsilyl group,a triethylsilyl group, a t-butyldimethylsilyl group, avinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilylgroup, a diphenylsilyl group, a phenylsilyl group and the like, but arenot limited thereto.

In the present specification, the fluorenyl group may be substituted,and adjacent substituents may bond to each other to form a ring.

When the fluorenyl group is substituted,

and the like may be included, however, the structure is not limitedthereto.

In the present specification, the heteroaryl group includes O, S, Se, Nor Si as a heteroatom, includes monocyclic or polycyclic having 2 to 60carbon atoms, and may be further substituted with other substituents.Herein, the polycyclic means a group in which the heteroaryl group isdirectly linked to or fused with other cyclic groups. Herein, the othercyclic groups may be a heteroaryl group, but may also be different typesof cyclic groups such as a cycloalkyl group, a heterocycloalkyl groupand an aryl group. The number of carbon atoms of the heteroaryl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 3 to 25. Specific examples of the heteroaryl group may include apyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group,a furanyl group, a thiophene group, an imidazolyl group, a pyrazolylgroup, an oxazolyl group, an isoxazolyl group, a thiazolyl group, anisothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolylgroup, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, apyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group,a thiazinyl group, a dioxynyl group, a triazinyl group, a tetrazinylgroup, a quinolyl group, an isoquinolyl group, a quinazolinyl group, anisoquinazolinyl group, a qninozolinyl group, a naphthyridyl group, anacridinyl group, a phenanthridinyl group, an imidazopyridinyl group, adiazanaphthalenyl group, a triazaindene group, an indolyl group, anindolizinyl group, a benzothiazolyl group, a benzoxazolyl group, abenzimidazolyl group, a benzothiophene group, a benzofuran group, adibenzothiophene group, a dibenzofuran group, a carbazolyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a phenazinyl group, adibenzosilole group, spirobi(dibenzosilole), a dihydrophenazinyl group,a phenoxazinyl group, a phenanthridyl group, an imidazopyridinyl group,a thienyl group, an indolo[2,3-a]carbazolyl group, anindolo[2,3-b]carbazolyl group, an indolinyl group, a10,11-dihydro-dibenzo[b,f]azepine group, a 9,10-dihydroacridinyl group,a phenanthrazinyl group, a phenothiathiazinyl group, a phthalazinylgroup, a naphthylidinyl group, a phenanthrolinyl group, abenzo[c][1,2,5]thiadiazolyl group, a5,10-dihydrobenzo[b,e][1,4]azasilinyl group, apyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, apyrido[1,2-a]imidazo[1,2-e]indolinyl group, a5,11-dihydroindeno[1,2-b]carbazolyl group and the like, but are notlimited thereto.

In the present specification, the phosphine oxide group may bespecifically substituted with an aryl group, and examples describedabove may be applied to the aryl group. Examples of the phosphine oxidegroup may include a diphenylphosphine oxide group, a dinaphthylphosphineoxide group and the like, but are not limited thereto.

In the present specification, the amine group may be selected from thegroup consisting of a monoalkylamine group; a monoarylamine group; amonoheteroarylamine group; —NH₂; a dialkylamine group; a diarylaminegroup; a diheteroarylamine group; an alkylarylamine group; analkylheteroarylamine group; and an arylheteroarylamine group, andalthough not particularly limited thereto, the number of carbon atoms ispreferably from 1 to 30. Specific examples of the amine group mayinclude a methylamine group, a dimethylamine group, an ethylamine group,a diethylamine group, a phenylamine group, a naphthylamine group, abiphenylamine group, a dibiphenylamine group, an anthracenylamine group,a 9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group, a biphenylnaphthylamine group, aphenylbiphenylamine group, a biphenylfluorenylamine group, aphenyltriphenylenylamine group, a biphenyltriphenylenylamine group andthe like, but are not limited thereto.

In the present specification, the structures illustrated as the arylgroup and the heteroaryl group described above may be used as thearylene group and the heteroarylene group except that they are not amonovalent group.

In the present specification, an “adjacent” group may mean a substituentsubstituting an atom directly linked to an atom substituted by thecorresponding substituent, a substituent sterically most closelypositioned to the corresponding substituent, or another substituentsubstituting an atom substituted by the corresponding substituent. Forexample, two substituents substituting ortho positions in a benzenering, and two substituents substituting the same carbon in an aliphaticring may be interpreted as groups “adjacent” to each other.

As an aliphatic or aromatic hydrocarbon ring or heteroring that adjacentgroups may form, the structures illustrated as the cycloalkyl group, theheterocycloalkyl group, the aryl group and the heteroaryl groupdescribed above may be applied except for those that are not amonovalent group.

One embodiment of the present specification provides a heterocycliccompound represented by Chemical Formula 1. Particularly, ChemicalFormula 1 has a structure in which dibenzofuran or dibenzothiophene isfused to quinoline, and HOMO and LUMO levels can be adjusted by havingvarious substituents in the benzene ring which is not fused to thequinoline in the dibenzofuran or dibenzothiophene. Accordingly,electrical properties of the structure may be enhanced by adjusting anenergy band gap. In addition, electron transfer capability of a materialmay be enhanced through substituents having strong electron migrationproperties.

In one embodiment of the present specification, X is O or S.

In one embodiment of the present specification, X is O.

In another embodiment, X is S.

In one embodiment of the present specification, L is a direct bond; asubstituted or unsubstituted C6 to C60 arylene group; or a substitutedor unsubstituted C2 to C60 heteroarylene group.

By the Z substituent and the core structure being separated by L in thecompound, hole migration properties of the core structure and electronmigration properties of the substituent are distinguished in theelectron cloud distribution of the molecule. This is an excellentbipolar structure facilitating electron migration, and therefore,efficiency, lifetime and driving voltage may be significantly improved.

In one embodiment of the present specification, L is a direct bond; asubstituted or unsubstituted C6 to C30 arylene group; or a substitutedor unsubstituted C2 to C30 heteroarylene group.

In one embodiment of the present specification, L is a direct bond; asubstituted or unsubstituted phenylene group; a substituted orunsubstituted biphenylene group; a substituted or unsubstitutedterphenylene group; a substituted or unsubstituted naphthylene group; asubstituted or unsubstituted anthracenylene group; a substituted orunsubstituted triphenylenylene group; a substituted or unsubstitutedphenanthrenylene group; a substituted or unsubstituted divalent pyridinegroup; a substituted or unsubstituted divalent pyrimidine group; or asubstituted or unsubstituted divalent triazine group.

In one embodiment of the present specification, L is a direct bond; aphenylene group unsubstituted or substituted with an aryl group or aheteroaryl group; a biphenylene group; a terphenylene group; anaphthylene group; an anthracenylene group; a triphenylenylene group; aphenanthrenylene group; a divalent pyridine group unsubstituted orsubstituted with an aryl group or a heteroaryl group; a divalentpyrimidine group unsubstituted or substituted with an aryl group; or adivalent triazine group unsubstituted or substituted with an aryl groupor a heteroaryl group.

In one embodiment of the present specification, L is a direct bond; aphenylene group unsubstituted or substituted with a phenyl group or acarbazole group; a biphenylene group; a terphenylene group; anaphthylene group; an anthracenylene group; a triphenylenylene group; aphenanthrenylene group; a divalent pyridine group unsubstituted orsubstituted with a phenyl group or a pyridine group; a divalentpyrimidine group unsubstituted or substituted with a phenyl group or abiphenyl group; or a divalent triazine group unsubstituted orsubstituted with a phenyl group unsubstituted or substituted with acyano group, a biphenyl group, a naphthyl group, or a carbazole groupunsubstituted or substituted with a phenyl group.

In one embodiment of the present specification, Z is a substituted orunsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynylgroup; a substituted or unsubstituted C3 to C60 cycloalkyl group; asubstituted or unsubstituted C2 to C60 heterocycloalkyl group; asubstituted or unsubstituted C6 to C60 aryl group; a substituted orunsubstituted C2 to C60 heteroaryl group; a substituted or unsubstitutedC1 to C20 alkylamine group; a substituted or unsubstituted C6 to C60arylamine group; a substituted or unsubstituted C2 to C60heteroarylamine group; or a substituted or unsubstituted phosphine oxidegroup.

In one embodiment of the present specification, Z is a substituted orunsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynylgroup; a substituted or unsubstituted C3 to C30 cycloalkyl group; asubstituted or unsubstituted C2 to C30 heterocycloalkyl group; asubstituted or unsubstituted C6 to C30 aryl group; a substituted orunsubstituted C2 to C30 heteroaryl group; a substituted or unsubstitutedC1 to C10 alkylamine group; a substituted or unsubstituted C6 to C30arylamine group; a substituted or unsubstituted C2 to C30heteroarylamine group; or a substituted or unsubstituted phosphine oxidegroup.

In one embodiment of the present specification, Z is a substituted orunsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 toC30 heteroaryl group; or a substituted or unsubstituted phosphine oxidegroup.

In one embodiment of the present specification, Z is a substituted orunsubstituted phenyl group; a biphenyl group; a terphenyl group; anaphthyl group; a triphenylenyl group; a phenanthrenyl group; ananthracenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group;a spirobifluorenyl group; an isoquinolinyl group; a quinazolinyl group;a phenoxazinyl group; a phenothiazinyl group; an indolocarbazole group;a substituted or unsubstituted pyridine group; a substituted orunsubstituted pyrimidine group; a substituted or unsubstituted triazinegroup; a substituted or unsubstituted carbazole group; a substituted orunsubstituted benzocarbazole group; a substituted or unsubstitutedphenanthrolinyl group; a substituted or unsubstituted dibenzofurangroup; a substituted or unsubstituted dibenzothiophene group; asubstituted or unsubstituted dihydroacridine group; or a substituted orunsubstituted phosphine oxide group.

In one embodiment of the present specification, Z is a phenyl groupunsubstituted or substituted with a cyano group, a phenyl group or acarbazole group; a biphenyl group; a terphenyl group; a naphthyl group;a triphenylenyl group; a phenanthrenyl group; an anthracenyl group; adimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenylgroup; an isoquinolinyl group; a quinazolinyl group; a phenoxazinylgroup; a phenothiazinyl group; an indolocarbazole group; a pyridinegroup unsubstituted or substituted with a phenyl group or a pyridinegroup; a pyrimidine group unsubstituted or substituted with a phenylgroup or a biphenyl group; a triazine group unsubstituted or substitutedwith a phenyl group unsubstituted or substituted with a naphthyl groupor a cyano group, a biphenyl group, a naphthyl group, adimethylfluorenyl group, a dibenzofuran group, a dibenzothiophene group,or a carbazole group unsubstituted or substituted with a phenyl group; acarbazole group unsubstituted or substituted with a phenyl group; abenzocarbazole group; a phenanthrolinyl group unsubstituted orsubstituted with a phenyl group; a dibenzofuran group unsubstituted orsubstituted with a phenyl group; a dibenzothiophene group unsubstitutedor substituted with a phenyl group; a dihydroacridine groupunsubstituted or substituted with a methyl group or a phenyl group; or aphosphine oxide group unsubstituted or substituted with a phenyl group.

In one embodiment of the present specification, R1 is a substituted orunsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynylgroup; a substituted or unsubstituted C3 to C60 cycloalkyl group; asubstituted or unsubstituted C2 to C60 heterocycloalkyl group; asubstituted or unsubstituted C6 to C60 aryl group; a substituted orunsubstituted C2 to C60 heteroaryl group; a substituted or unsubstitutedC1 to C20 alkylamine group; a substituted or unsubstituted C6 to C60arylamine group; a substituted or unsubstituted C2 to C60heteroarylamine group; or a substituted or unsubstituted phosphine oxidegroup.

In one embodiment of the present specification, R1 is a substituted orunsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60heterocycloalkyl group; a substituted or unsubstituted C6 to C60 arylgroup; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present specification, R1 is a substituted orunsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2to C60 heteroaryl group.

In one embodiment of the present specification, R1 is a substituted orunsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2to C30 heteroaryl group.

In one embodiment of the present specification, R1 is a substituted orunsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, R1 is a substituted orunsubstituted phenyl group; a substituted or unsubstituted naphthylgroup; a substituted or unsubstituted anthracenyl group; a substitutedor unsubstituted phenanthrenyl group; a substituted or unsubstitutedpyrenyl group; or a substituted or unsubstituted perylene group.

In one embodiment of the present specification, R1 is a phenyl group; anaphthyl group; an anthracenyl group; a phenanthrenyl group; a pyrenylgroup; or a perylene group.

In one embodiment of the present specification, R2 to R7 are eachindependently hydrogen; deuterium; a halogen group; a cyano group; asubstituted or unsubstituted C1 to C60 alkyl group; a substituted orunsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstitutedC6 to C60 aryl group; or a substituted or unsubstituted C2 to C60heteroaryl group.

In one embodiment of the present specification, R2 to R7 are eachindependently hydrogen; deuterium; a substituted or unsubstituted C1 toC60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; ora substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present specification, R2 to R7 are eachindependently hydrogen; or deuterium.

In one embodiment of the present specification, R2 to R7 are hydrogen.

In one embodiment of the present specification, m may be 1 or 2.

In one embodiment of the present specification, n may be an integer of 1to 5.

In one embodiment of the present specification, Chemical Formula 1 isrepresented by the following Chemical Formula 1-1.

In Chemical Formula 1-1, X, L, Z, R2 to R7, a, b, m and n have the samedefinitions as in Chemical Formula 1,

L′ is a direct bond; a substituted or unsubstituted C6 to C60 arylenegroup; or a substituted or unsubstituted C2 to C60 heteroarylene group,

Z′ is a substituted or unsubstituted C1 to C60 alkyl group; asubstituted or unsubstituted C3 to C60 cycloalkyl group; a substitutedor unsubstituted C2 to C60 heterocycloalkyl group; a substituted orunsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2to C60 heteroaryl group.

In one embodiment of the present specification, L′ is a direct bond.

In one embodiment of the present specification, Z′ is a substituted orunsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2to C60 heteroaryl group.

In one embodiment of the present specification, Z′ is a substituted orunsubstituted C6 to C60 aryl group.

In one embodiment of the present specification, Z′ is a substituted orunsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, Z′ is a phenyl group; anaphthyl group; an anthracenyl group; a phenanthrenyl group; a pyrenylgroup; or a perylene group.

In the heterocyclic compound provided in one embodiment of the presentspecification, Chemical Formula 1 is represented by any one of thefollowing Chemical Formulae 1-2 to 1-5.

In Chemical Formulae 1-2 to 1-5, X, L, Z, R1 to R7, a, b, m and n havethe same definitions as in Chemical Formula 1.

In the heterocyclic compound provided in one embodiment of the presentspecification, Chemical Formula 1 is represented by any one of thefollowing Chemical Formulae 2 to 4.

In Chemical Formulae 2 to 4,

X, L, Z, R1 to R7, a, b, m and n have the same definitions as inChemical Formula 1.

In one embodiment of the present specification, Chemical Formula 1 maybe represented by any one of the following compounds, but is not limitedthereto.

In addition, by introducing various substituents to the structure ofChemical Formula 1, compounds having unique properties of the introducedsubstituents may be synthesized. For example, by introducingsubstituents normally used as hole injection layer materials, holetransfer layer materials, light emitting layer materials, electrontransfer layer materials and charge generation layer materials used formanufacturing an organic light emitting device to the core structure,materials satisfying conditions required for each organic material layermay be synthesized.

In addition, by introducing various substituents to the structure ofChemical Formula 1, the energy band gap may be finely adjusted, and bythe high T1 value obtained therefrom, an organic light emitting devicewith superior efficiency may be provided.

One embodiment of the present specification provides an organic lightemitting device including a first electrode; a second electrode; and anorganic material layer provided between the first electrode and thesecond electrode, wherein the organic material layer includes theheterocyclic compound represented by Chemical Formula 1.

In one embodiment of the present specification, the first electrode maybe an anode, and the second electrode may be a cathode.

In another embodiment of the present specification, the first electrodemay be a cathode, and the second electrode may be an anode.

In one embodiment of the present specification, the organic lightemitting device may be a blue organic light emitting device, and theheterocyclic compound according to Chemical Formula 1 may be used as amaterial of the blue organic light emitting device. For example, theheterocyclic compound according to Chemical Formula 1 may be included ina host material of a light emitting layer of the blue organic lightemitting device.

In another embodiment of the present specification, the organic lightemitting device may be a green organic light emitting device, and theheterocyclic compound according to Chemical Formula 1 may be used as amaterial of the green organic light emitting device. For example, theheterocyclic compound according to Chemical Formula 1 may be included ina host material of a light emitting layer of the green organic lightemitting device.

In another embodiment of the present specification, the organic lightemitting device may be a red organic light emitting device, and theheterocyclic compound according to Chemical Formula 1 may be used as amaterial of the red organic light emitting device. For example, theheterocyclic compound according to Chemical Formula 1 may be included ina host material of a light emitting layer of the red organic lightemitting device.

Specific descriptions on the heterocyclic compound represented byChemical Formula 1 are the same as the descriptions provided above.

The organic light emitting device of the present specification may bemanufactured using common organic light emitting device manufacturingmethods and materials except that one or more of the organic materiallayers are formed using the heterocyclic compound described above.

The heterocyclic compound may be formed into an organic material layerthrough a solution coating method as well as a vacuum deposition methodwhen manufacturing the organic light emitting device. Herein, thesolution coating method means spin coating, dip coating, inkjetprinting, screen printing, a spray method, roll coating and the like,but is not limited thereto.

The organic material layer of the organic light emitting device of thepresent specification may be formed in a single layer structure, but maybe formed in a multilayer structure in which two or more organicmaterial layers are laminated. For example, the organic light emittingdevice of the present disclosure may have a structure including a holeinjection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer, an electron injection layer and the like as theorganic material layer. However, the structure of the organic lightemitting device is not limited thereto, and may include a smaller numberof organic material layers.

In the organic light emitting device of the present specification, theorganic material layer includes an electron transfer layer, and theelectron transfer layer may include the heterocyclic compound ofChemical Formula 1. When using the heterocyclic compound as an electrontransfer material, HOMO and LUMO may be adjusted depending on thesubstituent position, and excellent electron transfer efficiency isobtained. In addition, compared to existing electron transfer materials,migration of electrons in a reverse direction is prevented due to adifference in the T1 value, and as a result, superior device efficiencyis obtained.

The organic light emitting device of the present disclosure may furtherinclude one, two or more layers selected from the group consisting of alight emitting layer, a hole injection layer, a hole transfer layer, anelectron injection layer, an electron transfer layer, an electronblocking layer and a hole blocking layer.

FIG. 1 to FIG. 3 illustrate a lamination order of electrodes and organicmaterial layers of an organic light emitting device according to oneembodiment of the present specification. However, the scope of thepresent application is not limited to these diagrams, and structures oforganic light emitting devices known in the art may also be used in thepresent application.

FIG. 1 illustrates an organic light emitting device in which an anode(200), an organic material layer (300) and a cathode (400) areconsecutively laminated on a substrate (100). However, the structure isnot limited to such a structure, and as illustrated in FIG. 2, anorganic light emitting device in which a cathode, an organic materiallayer and an anode are consecutively laminated on a substrate may alsobe obtained.

FIG. 3 illustrates a case of the organic material layer being amultilayer. The organic light emitting device according to FIG. 3includes a hole injection layer (301), a hole transfer layer (302), alight emitting layer (303), an electron transfer layer (304) and anelectron injection layer (305). However, the scope of the presentapplication is not limited to such a lamination structure, and asnecessary, layers other than the light emitting layer may not beincluded, and other necessary functional layers may be further included.

The organic material layer including the heterocyclic compoundrepresented by Chemical Formula 1 may further include other materials asnecessary.

The organic light emitting device according to one embodiment of thepresent specification includes a first electrode; a first stack providedon the first electrode and including a first light emitting layer; acharge generation layer provided on the first stack; a second stackprovided on the charge generation layer and including a second lightemitting layer; and a second electrode provided on the second stack,wherein the charge generation layer may include the heterocycliccompound represented by Chemical Formula 1.

The organic light emitting device according to one embodiment of thepresent specification includes a first electrode; a second electrode;and an organic material layer provided between the first electrode andthe second electrode, wherein the organic material layer includes two ormore stacks, and the two or more stacks each independently include alight emitting layer, a charge generation layer is included between thetwo or more stacks, and the charge generation layer may include theheterocyclic compound represented by Chemical Formula 1.

The organic light emitting device according to one embodiment of thepresent specification includes a first electrode; a second electrode;and an organic material layer provided between the first electrode andthe second electrode, wherein the organic material layer includes afirst stack including a first light emitting layer; a charge generationlayer provided on the first stack; and a second stack including a secondlight emitting layer, and the charge generation layer may include theheterocyclic compound represented by Chemical Formula 1.

In addition, the organic light emitting device according to oneembodiment of the present specification includes an anode, a cathode,and two or more stacks provided between the anode and the cathode, thetwo or more stacks each independently include a light emitting layer, acharge generation layer is included between the two or more stacks, andthe charge generation layer includes the heterocyclic compoundrepresented by Chemical Formula 1.

In addition, the organic light emitting device according to oneembodiment of the present specification includes an anode, a first stackprovided on the anode and including a first light emitting layer, acharge generation layer provided on the first stack, a second stackprovided on the charge generation layer and including a second lightemitting layer, and a cathode provided on the second stack. Herein, thecharge generation layer may include the heterocyclic compoundrepresented by Chemical Formula 1. When the heterocyclic compound isincluded in the charge generation layer, superior efficiency as a chargegeneration layer material is obtained by an electron-friendlysubstituent structure and a hole migration-friendlyquinoline-dibenzofuran or quinoline-dibenzothiophene fused structure.

The organic light emitting device according to one embodiment of thepresent specification includes a first electrode; a first stack providedon the first electrode and including a first light emitting layer; acharge generation layer provided on the first stack; a second stackprovided on the charge generation layer and including a second lightemitting layer; and a second electrode provided on the second stack,wherein the charge generation layer is an N-type charge generationlayer, and the charge generation layer may include the heterocycliccompound represented by Chemical Formula 1.

In addition, the first stack and the second stack may each independentlyfurther include one or more types of the hole injection layer, the holetransfer layer, the hole blocking layer, the electron transfer layer,the electron injection layer and the like described above.

The charge generation layer may be an N-type charge generation layer ora P-type charge generation layer, and the charge generation layer mayfurther include a dopant known in the art in addition to theheterocyclic compound represented by Chemical Formula 1.

As the organic light emitting device according to one embodiment of thepresent specification, an organic light emitting device having a 2-stacktandem structure is illustrated in FIG. 4.

Herein, the first electron blocking layer, the first hole blockinglayer, the second hole blocking layer and the like described in FIG. 4may not be included in some cases.

In the organic light emitting device according to one embodiment of thepresent specification, materials other than the heterocyclic compoundrepresented by Chemical Formula 1 are illustrated below, however, theseare for illustrative purposes only and not for limiting the scope of thepresent application, and the materials may be replaced by materialsknown in the art.

As the anode material, materials having relatively large work functionmay be used, and transparent conductive oxides, metals, conductivepolymers or the like may be used. Specific examples of the anodematerial include metals such as vanadium, chromium, copper, zinc andgold, or alloys thereof; metal oxides such as zinc oxide, indium oxide,indium tin oxide (ITO) and indium zinc oxide (IZO); combinations ofmetals and oxides such as ZnO:Al or SnO₂:Sb; conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT),polypyrrole and polyaniline, and the like, but are not limited thereto.

As the cathode material, materials having relatively small work functionmay be used, and metals, metal oxides, conductive polymers or the likemay be used. Specific examples of the cathode material include metalssuch as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al or LiO₂/Al, andthe like, but are not limited thereto.

As the hole injection material, known hole injection materials may beused, and for example, phthalocyanine compounds such as copperphthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-typeamine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA),4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB)described in the literature [Advanced Material, 6, p. 677 (1994)],polyaniline/dodecylbenzene sulfonic acid,poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate),polyaniline/camphor sulfonic acid orpolyaniline/poly(4-styrenesulfonate) that are conductive polymers havingsolubility, and the like, may be used.

As the hole transfer material, pyrazoline derivatives, arylamine-basedderivatives, stilbene derivatives, triphenyldiamine derivatives and thelike may be used, and low molecular or high molecular materials may alsobe used.

As the electron transfer material, metal complexes of oxadiazolederivatives, anthraquinodimethane and derivatives thereof, benzoquinoneand derivatives thereof, naphthoquinone and derivatives thereof,anthraquinone and derivatives thereof, tetracyanoanthraquinodimethaneand derivatives thereof, fluorenone derivatives, diphenyldicyanoethyleneand derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinolineand derivatives thereof, and the like, may be used in addition to theheterocyclic compound, and high molecular materials may also be used aswell as low molecular materials.

As examples of the electron injection material, LiF is typically used inthe art, however, the present application is not limited thereto.

As the light emitting material, red, green or blue light emittingmaterials may be used, and as necessary, two or more light emittingmaterials may be mixed and used. Herein, two or more light emittingmaterials may be used by being deposited as individual sources of supplyor by being premixed and deposited as one source of supply. In addition,fluorescent materials may also be used as the light emitting material,however, phosphorescent materials may also be used. As the lightemitting material, materials emitting light by bonding electrons andholes injected from an anode and a cathode, respectively, may be usedalone, however, materials having a host material and a dopant materialinvolving in light emission together may also be used.

When mixing light emitting material hosts, same series hosts may bemixed, or different series hosts may be mixed. For example, any two ormore types of materials among n-type host materials or p-type hostmaterials may be selected and used as a host material of a lightemitting layer.

The organic light emitting device according to one embodiment of thepresent specification may be a top-emission type, a bottom-emission typeor a dual-emission type depending on the materials used.

The heterocyclic compound according to one embodiment of the presentspecification may also be used in an organic electronic device includingan organic solar cell, an organic photo conductor, an organic transistorand the like under a similar principle used in the organic lightemitting device.

Hereinafter, the present specification will be described in more detailwith reference to examples, however, these are for illustrative purposesonly, and the scope of the present application is not limited thereto.

[Preparation Example 1] Preparation of Compound 4

1) Preparation of Compound 1-1

After dissolving 1-bromo-8-chlorodibenzo[b,d]furan (100 g, 0.3552 mol)and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (77.8 g,0.3552 mol) in toluene, ethanol and H₂O (2000 mL:200 mL:200 mL),Pd(PPh₃)₄ (tetrakis(triphenylphosphine)palladium(0)) (20.5 g, 0.017 mol)and NaHCO₃ (89 g, 1.06 mol) were introduced thereto, and the result wasstirred for 3 hours at 100° C. After the reaction was completed,methylene chloride (MC) and distilled water were introduced to thereaction solution, and the result was extracted, then dried withanhydrous MgSO₄, and the solvent was removed using a rotary evaporatorto obtain Compound 1-1 (77 g, 74%) in a liquid form.

2) Preparation of Compound 1-2

Compound 1-1 (77 g, 0.262 mol) and triethylamine (86 mL, 0.393 mol) wereintroduced to methylene chloride (1200 mL) and dissolved therein. To themixture, benzoyl chloride (55 g, 0.393 mol) dissolved in methylenechloride (300 mL) was slowly added dropwise at 0° C. After the reactionwas completed, white solids in the reaction solution were filtered andwashed with hexane. These were dried to obtain Compound 1-2 (86 g, 83%)in a solid form.

3) Preparation of Compound 1-3

After dissolving Compound 1-2 (86 g, 0.216 mol) in nitrobenzene (1500mL), POCl₃ (30 mL, 0.324 mol) was slowly added dropwise thereto, and theresult was reacted for 15 hours at 140° C. After the reaction wascompleted, a solution obtained by dissolving NaHCO₃ in distilled waterwas slowly introduced to the reaction solution, and the result wasstirred. Solids produced after that were filtered and collected, and thecollected solids were recrystallized in MC and MeOH to obtain Compound1-3 (41 g, 51%) in a solid form.

4) Preparation of Compound 1-4

After dissolving Compound 1-3 (41 g, 0.1079 mol) in 1,4-dioxane (800mL), Pd₂(dba)₃ (tris(dibenzylideneacetone)dipalladium(0)) (9.8 g, 0.0107mol), XPhos (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) (5.1g, 0.0107 mol) and KOAc (potassium acetate) (31 g, 0.3237 mol) weredissolved therein, and the result was reacted for 4 hours at 90° C.After the reaction was completed, water and methylene chloride wereintroduced to the reaction solution, and the result was extracted.Solids obtained after that were dried, and recrystallized with methylenechloride and methanol to obtain Compound 1-4 (30 g, 60%) in a solidform.

5) Preparation of Compound 4

After dissolving Compound 1-4 (6.4 g, 0.017 mol) and2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.4 g, 0.017 mol) in1,4-dioxane:H₂O=100 mL:20 mL, Pd(PPh₃)₄ (1.96 g, 0.0017 mol) and K₃PO₄(20.8 g, 0.051 mol) were introduced thereto, and the result was stirredfor 5 hours at 100° C. After the reaction was completed, solids producedin the reaction solution were washed with 1,4-dioxane and H₂O. Afterthat, only the solids were purified using a recrystallization method indichlorobenzene (DCB) to obtain Compound 4 (6.6 g, 60%). [PreparationExample 2] Preparation of Compound 88

1) Preparation of Compound 1-1

Compound 1-1 was the same as Compound 1-1 of Preparation Example 1.

2) Preparation of Compound 2-2

Compound 1-1 (77 g, 0.262 mol) and triethylamine (86 mL, 0.393 mol) wereintroduced to MC (1200 mL) and dissolved therein. To the mixture,1-pyrenecarbonyl chloride (104 g, 0.393 mol) dissolved in methylenechloride (300 mL) was slowly added dropwise at 0° C. After the reactionwas completed, white solids in the reaction solution were filtered andwashed with hexane. These were dried to obtain Compound 2-2 (75 g, 67%)in a solid form.

3) Preparation of Compound 2-3

After dissolving Compound 2-2 (86 g, 0.143 mol) in nitrobenzene (1500mL), POCl₃ (20 mL, 0.215 mol) was slowly added dropwise thereto, and theresult was reacted for 15 hours at 140° C. After the reaction wascompleted, a solution obtained by dissolving NaHCO₃ in distilled waterwas slowly introduced to the reaction solution, and the result wasstirred. Solids produced after that were filtered and collected, and thecollected solids were recrystallized in methylene chloride and methanolto obtain Compound 2-3 (29 g, 41%) in a solid form.

4) Preparation of Compound 2-4

After dissolving Compound 2-3 (29 g, 0.057 mol) in 1,4-dioxane (800 mL),Pd₂(dba)₃ (5.2 g, 0.0057 mol), XPhos (2.7 g, 0.0057 mol) and KOAc (16.7g, 0.171 mol) were dissolved therein, and the result was reacted for 4hours at 90° C. After the reaction was completed, water and MC wereintroduced to the reaction solution, and the result was extracted. Afterthat, solids obtained by drying the result were recrystallized withmethylene chloride and methanol to obtain Compound 2-4 (20 g, 60%) in asolid form.

5) Preparation of Compound 88

After dissolving Compound 2-4 (10 g, 0.017 mol) and4-(3-bromophenyl)dibenzo[b,d]thiophene (5.7 g, 0.017 mol) in1,4-dioxane:H₂O=100 mL:20 mL, Pd(PPh₃)₄ (1.96 g, 0.0017 mol) and K₃PO₄(20.8 g, 0.051 mol) were introduced thereto, and the result was stirredfor 5 hours at 100° C. After the reaction was completed, solids producedin the reaction solution were washed with 1,4-dioxane and H₂O. Afterthat, only the solids were purified using a recrystallization method indichlorobenzene (DCB) to obtain Compound 88 (4.9 g, 40%).

Target compounds were synthesized in the same manner as in PreparationExample 1 except that Intermediate A of the following Table 1 was usedinstead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 1 Com- pound Intermediate A Target Compound Yield  1

61%  5

62%  7

51%  8

60%  9

61%  11

62%  12

51%  13

60%  15

61%  16

62%  17

51%  18

60%  24

61%  25

62%  28

51%  30

60%  35

61%  36

62%  37

51%  38

60%  41

61%  42

62%  44

51%  45

60%  47

61%  52

62%  53

51%  56

60%  57

61%  64

62%  68

51%  69

60%  70

61%  72

62%  75

51%  77

60%  79

61%  80

62%  84

51%  86

60%  89

62%  91

51%  92

60%  97

61% 100

62% 102

51% 103

60% 107

61% 112

62% 113

51% 114

60% 116

61% 119

62% 120

51% 132

62% 133

51% 135

60% 139

61% 140

62% 141

51% 142

60%

Target compounds were synthesized in the same manner as in PreparationExample 2 except that Intermediate 1 of the following Table 2 was usedinstead of 1-pyrenecarbonyl chloride, and Intermediate B of thefollowing Table 2 was used instead of4-(3-bromophenyl)dibenzo[b,d]thiophene.

TABLE 2 Intermediate B Intermediate 1 Target Compound 121

60% 128

61%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 6-bromo-2-chlorodibenzo[b,d]furan was used insteadof 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate C of thefollowing Table 3 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 3 Compound Intermediate C Target Compound Yield  58

62% 156

65% 157

65% 159

62% 161

51% 165

60% 166

61% 170

62% 171

65% 172

65% 173

62% 178

60% 179

61% 180

60% 185

62% 187

65% 190

65% 191

62% 192

51% 194

60% 195

61% 196

60% 200

55%

Target compounds were synthesized in the same manner as in PreparationExample 2 except that Intermediate 2 of the following Table 4 was usedinstead of 1-pyrenecarbonyl chloride, 6-bromo-2-chlorodibenzo[b,d]furanwas used instead of 1-bromo-8-chlorodibenzo[b,d]furan, and IntermediateD of the following Table 4 was used instead of 4-3bromophenyl)dibenzo[b,d]thiophene.

TABLE 4 Intermediate D Intermediate 2 Target Compound 168

60% 176

61%

A target compound was synthesized in the same manner as in PreparationExample 1 except that 2-bromo-8-chlorodibenzo[b,d]furan was used insteadof 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate E of thefollowing Table 5 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 5 Compound Intermediate E Target Compound Yield 149

52%

A target compound was synthesized in the same manner as in PreparationExample 2 except that Intermediate 3 of the following Table 6 was usedinstead of 1-pyrenecarbonyl chloride, 2-bromo-8-chlorodibenzo[b,d]furanwas used instead of 1-bromo-8-chlorodibenzo[b,d]furan, and IntermediateF of the following Table 6 was used instead of4-(3-bromophenyl)dibenzo[b,d]thiophene.

TABLE 6 Compound Intermediate F Intermediate 3 Target Compound Yield 145

53%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 1-bromo-6-chlorodibenzo[b,d]furan was used insteadof 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate G of thefollowing Table 7 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 7 Compound Intermediate G Target Compound Yield 384

53% 386

62% 387

65% 388

65% 392

62% 395

51% 396

60% 397

61% 399

60% 400

62% 401

65% 404

65% 408

51% 409

60% 411

61% 413

60% 415

62% 416

65% 417

65%

A target compound was synthesized in the same manner as in PreparationExample 2 except that Intermediate 4 of the following Table 8 was usedinstead of 1-pyrenecarbonyl chloride, 1-bromo-6-chlorodibenzo[b,d]furanwas used instead of 1-bromo-8-chlorodibenzo[b,d]furan, and IntermediateH of the following Table 8 was used instead of 4-3bromophenyl)dibenzo[b,d]thiophene.

TABLE 8 Compound Intermediate H Intermediate 4 Target Compound Yield 407

53%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 4,6-dibromodibenzo[b,d]furan was used instead of1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate I of the followingTable 9 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 9 Com- pound Intermediate I Target Compound Yield 421

53% 423

62% 424

65% 426

65% 431

62% 432

51% 433

60% 436

61% 438

60% 440

62% 441

65% 443

65% 447

62% 448

51% 449

60% 450

61% 452

60% 456

62% 460

65% 462

65% 465

62% 467

51% 470

61% 475

60% 476

62% 477

65% 479

65% 481

62% 482

51% 485

60% 488

61% 489

60% 490

62% 493

65% 494

65% 495

62% 500

51% 504

60% 505

61% 506

60% 507

62% 512

65% 513

65% 516

62% 517

51% 518

60% 519

61% 520

60% 524

65% 525

65% 527

62% 528

51% 531

60% 532

61% 533

60% 535

62% 536

65% 539

65% 542

62% 543

51% 544

60% 547

61% 549

62% 550

65%

Target compounds were synthesized in the same manner as in PreparationExample 2 except that Intermediate 5 of the following Table 10 was usedinstead of 1-pyrenecarbonyl chloride, 4,6-dibromodibenzo[b,d]furan wasused instead of 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate I ofthe following Table 10 was used instead of4-(3-bromophenyl)dibenzo[b,d]thiophene.

TABLE 10 Com- Intermediate Intermediate pound I 5 Target Compound Yield468

53% 522

52% 548

50%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 1-chloro-6-fluorodibenzo[b,d]furan was usedinstead of 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate J of thefollowing Table 11 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 11 Com- pound Intermediate J Target Compound Yield 554

53% 555

62% 557

65% 558

65% 564

62% 565

51% 566

60% 569

61% 573

60% 574

62% 580

65% 583

65% 584

62% 585

51% 587

60% 588

61% 594

60%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 7-chloro-1-fluorodibenzo[b,d]furan was usedinstead of 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate K of thefollowing Table 12 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 12 Com- pound Intermediate K Target Compound Yield 597

53% 598

62% 599

65% 600

65% 601

62% 605

51% 606

60% 611

61% 612

60% 615

51% 618

50%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 1-bromo-8-chlorodibenzo[b,d]thiophene was usedinstead of 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate L of thefollowing Table 13 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 13 Compound Intermediate L Target Compound Yield 623

62% 624

65% 626

65% 629

62% 632

51% 634

60% 635

61% 636

60% 640

62% 641

65% 644

65% 646

62% 649

51% 651

60% 652

61% 653

60% 654

62% 655

65% 657

65% 659

62% 660

51% 661

60% 664

61% 665

60% 666

62% 670

65% 674

62% 675

51% 677

60% 680

61% 682

60% 685

65% 687

65% 688

62% 691

51% 695

61% 696

62% 697

65% 700

65% 704

51% 707

60% 708

62% 709

65% 713

65% 714

62% 716

51% 717

60% 721

61% 728

60% 729

62% 731

65% 732

65% 733

62% 734

51% 735

60% 736

61% 741

60% 743

62% 745

65% 748

65% 752

51% 756

60% 757

61% 761

60%

Target compounds were synthesized in the same manner as in PreparationExample 2 except that Intermediate 6 of the following Table 14 was usedinstead of 1-pyrenecarbonyl chloride,1-bromo-8-chlorodibenzo[b,d]thiophene was used instead of1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate M of the followingTable 14 was used instead of 4-(3-bromophenyl)dibenzo[b,d]thiophene.

TABLE 14 Compound Intermediate M Intermediate 6 Target Compound Yield620

53% 672

62% 683

60% 692

60% 703

62% 750

52%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 2-bromo-8-chlorodibenzo[b,d]thiophene was usedinstead of 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate N of thefollowing Table 15 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 15 Compound Intermediate N Target Compound Yield 764

53% 766

62% 767

65% 769

65%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 6-bromo-2-chlorodibenzo[b,d]thiophene was usedinstead of 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate O of thefollowing Table 16 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 16 Compound Intermediate O Target Compound Yield 771

62% 773

62% 775

65% 783

62% 784

51% 787

61% 789

60% 791

62% 792

65% 793

65% 798

62% 801

51% 802

60% 807

61% 809

60% 810

62% 814

65% 816

65% 817

62% 818

51% 822

60% 823

61% 829

62% 830

65% 831

65% 833

62% 836

51% 837

60% 838

61% 842

60% 844

62% 847

65% 848

65% 849

62% 858

51% 860

60% 861

61% 862

60% 863

62% 870

65% 871

65% 872

62% 883

51% 884

60% 887

61% 888

60% 890

62% 893

65% 905

65% 908

62% 910

51% 911

60%

Target compounds were synthesized in the same manner as in PreparationExample 2 except that Intermediate 7 of the following Table 17 was usedinstead of 1-pyrenecarbonyl chloride,6-bromo-2-chlorodibenzo[b,d]thiophene was used instead of1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate P of the followingTable 17 was used instead of 4-(3-bromophenyl)dibenzo[b,d]thiophene.

TABLE 17 Com- pound Intermediate P Intermediate 7 Target Compound Yield779

56% 786

56% 825

60%

Target compounds were synthesized in the same manner as in PreparationExample 1 except that 1-bromo-6-chlorodibenzo[b,d]thiophene was usedinstead of 1-bromo-8-chlorodibenzo[b,d]furan, and Intermediate Q of thefollowing Table 18 was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

TABLE 18 Com- pound Intermediate Q Target Compound Yield 916

53% 918

62% 919

65% 920

65% 923

62% 924

51% 930

60% 931

61% 932

62% 943

65% 945

65% 952

62% 955

51% 956

60% 957

62% 960

65% 963

65% 965

62% 968

51% 971

62% 979

65% 980

65% 984

62% 986

65% 998

65% 991

62% 995

51% 1000

60% 1004

61% 1006

60% 1011

62% 1015

65%

Synthesis identification results for the compounds prepared as above areshown in the following Table 19.

TABLE 19 Compound FD-MS Compound FD-MS 1 m/z = 576.65 4 m/z = 652.75(C40H24N4O = 576.195) (C46H28N4O = 652.226) 5 m/z = 728.85 7 m/z =804.95 (C52H32N4O = 728.25) (C58H36N4O = 804.28) 8 m/z = 728.85 9 m/z =804/95 (C52H32N4O = 728.25) (C58H36N4O = 804.28) 11 m/z = 666.74 12 m/z= 682.80 (C46H26N4O2 = 666.20) (C46H26N4OS = 682.18) 13 m/z = 741.85 15m/z = 665.75 (C52H31N5O = 741.25) (C46H27N5O = 665.22) 16 m/z = 742.8317 m/z = 792.80 (C52H30N4O = 742.23) (C56H32N4O2 = 792.25) 18 m/z =842.95 24 m/z = 571.67 (C60H34N4O2 = 842.26) (C43H25NO = 571.19) 25 m/z= 521/61 28 m/z = 577.70 (C39H23NO = 521.17) (C41H23NOS = 577.15) 30 m/z= 628.77 35 m/z = 818.93 (C46H32N2O = 628.25) (C58H34N4O2 = 818.26) 36m/z = 818.93 37 m/z = 752.92 (C58H34N4O2 = 818.26) (C56H36N2O = 752.28)38 m/z = 599/69 41 m/z = 725.85 (C43H25N3O = 599.2) (C53H1N3O = 725.24)42 m/z = 652.75 44 m/z = 659.78 (C46H28N4O = 652.22) (C50H29NO = 659.22)45 m/z = 621.67 47 m/z = 549.63 (C43H28NO2P = 621.18) (C39H23N3O =549.18) 52 m/z = 618.75 53 m/z = 660.77 (C43H26N2OS = 618.17) (C49H28N2O= 660.22) 56 m/z = 751.88 57 m/z = 834.99 (C55H33N3O = 751.26)(C58H34N4OS = 834.24) 58 m/z = 758.89 64 m/z = 804.95 (C52H30N4OS =758.21) (C58H36N4O = 804.28) 68 m/z = 732.86 69 m/z = 732.86 (C50H28N4OS= 732.19) (C50H28N4OS = 732.19) 70 m/z = 868.01 72 m/z = 690.76(C62H37N5O = 867.30) (C47H26N6O = 690.21) 75 m/z = 742.83 77 m/z =758.89 (C52H30N4O2 = 742.23) (C52H30N4OS = 758.21) 79 m/z = 768.92 80m/z = 741.85 (C55H36N4O = 768.28) (C5231N5O = 741.25) 84 m/z = 660.77 86m/z = 597.71 (C49H28N2O = 660.22) (C45H27NO = 597.20) 88 m/z = 727.88 89m/z = 663.77 (C53H29NOS = 727.19) (C49H29NO2 = 663.22) 91 m/z = 752.9192 m/z = 675.79 (C56H36N2O = 752.28) (C49H29N3O = 675.23) 97 m/z =575.67 100 m/z = 727.86 (C41H25N3O = 575.20) (C53H33N3O = 727.26) 102m/z = 701.82 103 m/z = 727.86 (C51H31N3O = 701.24) (C53H33N3O = 727.26)107 m/z = 727.86 112 m/z = 681.81 (C53H33N3O = 727.26) (C47H27N3OS =681.18) 113 m/z = 740.86 114 m/z = 691.83 (C53H32N4O = 740.25)(C50H33N3O = 691.26) 116 m/z = 741.85 119 m/z = 817.99 (C53H31N3O2 =741.24) (C60H39N3O = 817.30) 120 m/z = 740.86 121 m/z = 725.85(C53H32N4O = 740/25) (C53H31N3O = 725.24) 128 m/z = 777.92 132 m/z =681.81 (C57H35N3O = 777.27) (C47H27N3OS = 681.18) 133 m/z = 681.81 135m/z = 664.76 (C47H27N3OS = 681.18) (C47H28N4O = 664.22) 139 m/z = 757.91140 m/z = 816.96 (C53H31N3OS = 757.21) (C59H36N4O = 816.28) 141 m/z =767.93 142 m/z = 740/86 (C56H37N3O = 767.29) (C53H32N4O = 740.25) 145m/z = 702.81 149 m/z = 728.85 (C50H30N4O = 702.24) (C52H32N4O = 728.25)156 m/z = 652.75 157 m/z = 652.75 (C46H26N4O = 652.22) (C46H28N4O =652.22) 159 m/z = 804.95 161 m/z = 666.74 (C58H36N4O = 804.28)(C46H26N4O2 = 666.20) 165 m/z = 682.80 166 m/z = 741.85 (C46H26N4OS =682.18) (C52H31N5O = 741.25) 168 m/z = 715.81 170 m/z = 842.95(C50H29N4O = 715.23) (C60H34N4O2 = 842.26) 171 m/z = 758.89 172 m/z =817.95 (C52H30N4OS = 758.21) (C58H35N5O = 817.28) 173 m/z = 768.92 176m/z = 571.67 (C55H36N4O = 768.28) (C43H25NO = 571.19) 178 m/z = 573.69179 m/z = 527.64 (C43H27NO = 573.20) (C37H21NOS = 527.13) 180 m/z =552.67 185 m/z = 895.03 (C40H28N2O = 552.22) (C64H38N4O2 = 894.29) 187m/z = 676.81 190 m/z = 675.79 (C50H32N2O = 676.25) (C49H29N3O = 675.23)191 m/z = 725.85 192 m/z = 652.75 (C53H31N3O = 725.24) (C46H28N4O =652.22) 194 m/z = 659.78 195 m/z = 548.64 (C50H29NO = 659.22) (C40H24N2O= 548.18) 196 m/z = 625.73 200 m/z = 659.78 (C45H27N3O = 625.21)(C50H29NO = 659.22) 202 m/z = 660.77 204 m/z = 802.93 (C49H28N2O =660.22) (C58H34N4O = 802.27) 207 m/z = 728.85 210 m/z = 742.83(C52H32N4O = 728.25) (C52H30N4O2 = 742.23) 213 m/z = 732.86 214 m/z =868.01 (C50H28N4OS = 732.19) (C62H37N5O = 867.30) 216 m/z = 717.83 217m/z = 690.76 (C50H31N5O = 717.25) (C47H26N6O = 690.21) 220 m/z = 742.83222 m/z = 758.89 (C52H30N4O2 = 742.23) (C52H30N4OS = 758.21) 223 m/z =817.95 224 m/z = 768.92 (C58H35N5O = 817.28) (C55H36N4O = 768.28) 225m/z = 741.85 227 m/z = 602.69 (C52H31N5O = 741.25) (C43H26N2O2 = 602.19)228 m/z = 618.75 229 m/z = 660.77 (C43H26N2OS = 618.17) (C49H26N2O =660.22) 233 m/z = 911.09 237 m/z = 675.79 (C64H38N4OS = 910.27)(C49H29N3O = 675.23) 240 m/z = 662.79 243 m/z = 651.76 (C49H30N2O =662.23) (C47H29N3O = 651.23) 245 m/z = 651.76 247 m/z = 651.76(C47H29N3O = 651.23) (C47H29N3O = 651.23) 249 m/z = 803.96 251 m/z =715.81 (C59H37N3O = 803.29) (C51H29N3O2 = 715.22) 256 m/z = 740.86 257m/z = 691.83 (C53H32N4O = 740.25) (C50H33N3O = 691.26) 259 m/z = 791.91260 m/z = 741.85 (C57H33N3O2 = 791.25) (C53H31N3O2 = 741.24) 262 m/z =757.91 265 m/z = 767.93 (C53H31N3OS = 757.21) (C56H37N3O = 767.29) 266m/z = 740.86 267 m/z = 575.57 (C53H32N4O = 740.25) (C41H25N3O = 575.20)269 m/z = 727.86 271 m/z = 727.86 (C53H33N3O = 727.26) (C53H33N3O =727.26) 272 m/z = 803.96 273 m/z = 727.86 (C59H37N3O = 803.29)(C53H33N3O = 727.26) 274 m/z = 841.97 276 m/z = 665.75 (C61H35N3O2 =841.27) (C47H27N3O2 = 665.21) 277 m/z = 681.81 279 m/z = 740.86(C47H27N3OS = 681.18) (C53H32N4O = 740.25) 281 m/z = 664.76 284 m/z =741.85 (C47H28N4O = 662.22) (C53H31N3O2 = 741.24) 285 m/z = 757.91 287m/z = 816.96 (C53H31N3OS = 752.21) (C59H36N4O = 816.28) 288 m/z = 767.93292 m/z = 728.85 (C56H37N3O = 767.29) (C52H32N4O = 728.25) 294 m/z =855.01 296 m/z = 652.75 (C62H38N4O = 854.30) (C46H28N4O = 652.22) 299m/z = 682.80 302 m/z = 665.75 (C46H26N4OS = 682.18) (C46H27CN5O =665.22) 304 m/z = 742.83 305 m/z = 758/89 (C52H30N4O2 = 742.23)(C52H30N4OS = 758.21 307 m/z = 817.95 308 m/z = 768.92 (C58H35N4O =817.28) (C55H36N4O = 768.28) 309 m/z = 741.85 310 m/z = 571.67(C52H31N5O = 741.25) (C43H25NO = 571.19) 312 m/z = 597.71 313 m/z =753.69 (C45H27NO = 597.20) (C43H27NO = 573.20) 315 m/z = 521.61 316 m/z= 597.71 (C39H23NO = 521.17) (C45H27NO = 597.20) 318 m/z = 603.73 319m/z = 742.83 (C43H25NOS = 603.16) (C52H30N4O2 = 742.23) 322 m/z = 752.91325 m/z = 675.79 (C56H36N2O = 752.28) (C49H29N3O = 675.23) 326 m/z =725.85 327 m/z = 652.75 (C53H31N3O = 725.24) (C46H28N4O = 652.22) 329m/z = 548.64 331 m/z = 636.75 (C40H24N2O = 548.18) (C47H28N2O = 636.22)332 m/z = 662.79 336 m/z = 752.87 (C49H30N2O = 662.23) (C54H32N4O =752.25) 337 m/z = 751.88 338 m/z = 693.86 (C55H33N3O = 751.26)(C49H31N3S = 693.22) 339 m/z = 691.85 342 m/z = 728.85 (C49H29N3S =691.20) (C52H32N4O = 728.25) 343 m/z = 778.91 345 m/z = 868.01(C56H34N4O = 778.27) (C62H37N5O = 867.30) 348 m/z = 782.92 350 m/z =717.83 (C54H30N4OS = 782.21) (C50H31N5O = 717.25) 353 m/z = 742.83 355m/z = 758.89 (C52H30N4O2 = 742.23) (C52H30N4OS = 758.21) 358 m/z =768.92 359 m/z = 741.85 (C55H36N4O = 768.28) (C52H31N4O = 741.25) 360m/z = 628.77 364 m/z = 597.71 (C46H32N2O = 628.25) (C45H27NO = 597.20)365 m/z = 652.75 367 m/z = 945.09 (C46H28N4O = 652.22) (C68H40N4O2 =944.31) 368 m/z = 713.83 373 m/z = 712.85 (C53H31NO2 = 713.23)(C53H32N2O = 712.25) 374 m/z = 735.88 377 m/z = 727.86 (C56H33NO =735.25) (C53H33N3O = 727.26) 378 m/z = 803.95 379 m/z = 751.88(C59H27N3O = 803.29) (C55H33N3O = 751.26) 380 m/z = 727.86 384 m/z =665.75 (C53H33N3O = 727.26) (C47H27N3O2 = 665.21) 386 m/z = 731.87 387m/z = 740.86 (C51H29N3OS = 731.20) (C53H32N4O = 740/25) 388 m/z = 691.83392 m/z = 741.85 (C50H33N3O = 691.26) (C53H31N3O2 = 741.24) 395 m/z =917.08 396 m/z = 740.86 (C67H40N4O = 916.32) (C53H32N4O = 740.25) 397m/z = 651.76 399 m/z = 803.96 (C47H2N3O = 651.23) (C59H37N3O = 803.29)400 m/z = 651.76 401 m/z = 727.86 (C47H29N3O = 651.23) (C53H33N3O =727.26) 404 m/z = 665.75 407 m/z = 805.95 (C47H27N3O2 = 665.21)(C57H31N3OS = 805.21) 408 m/z = 740.86 409 m/z = 691.83 (C53H32N4O =740.25) (C50H33N3O = 691.25) 411 m/z = 741.85 413 m/z = 741.85(C53H31N3O2 = 741.24) (C53H31N3O2 = 741.24) 415 m/z = 757.91 416 m/z =816.96 (C53H31N3OS = 757.21) (C59H36N4O = 816.28) 417 m/z = 767.93 421m/z = 804.95 (C56H37N3O = 767.29) (C58H36N4O = 804.28) 423 m/z = 702.81424 m/z = 652.75 (C50H30N40 = 702.24) (C46H26N4O = 652.22) 426 m/z =778.91 431 m/z = 682.80 (C56H34N4O = 778.27) (C46H26N4OS = 682.18) 432m/z = 741.85 433 m/z = 692.82 (C52H31N5O = 741.25 (C49H32N4O = 692.25)436 m/z = 742.83 438 m/z = 758.89 (C52H30N4O2 = 742.23) (C52H30N4OS =758.21) 440 m/z = 741.85 441 m/z = 571.67 (C52H31N5O = 741.25) (C43H25NO= 571.19) 443 m/z = 597.71 447 m/z = 628.77 (C54H27NO = 597.20)(C46H32N2O = 628.25) 448 m/z = 597.71 449 m/z = 649.79 (C45H27NO =597.20) (C49H31NO = 649.24) 450 m/z = 911.09 452 m/z = 665.75(C64H38N4OS = 910.27) (C47H27N3O2 = 665.21) 456 m/z = 675.79 460 m/z =659.78 (C49H29N3O = 675.23) (C50H29NO = 659.22) 462 m/z = 548.64 465 m/z= 636.75 (C40H24N2O = 548.18) (C47H28N2O = 636.22) 467 m/z = 659.78 468m/z = 652.75 (C50H29NO = 659.22) (C47H28N2O = 652.21) 470 m/z = 752.87475 m/z = 728.85 (C54H32N4O = 752.25) (C52H32N4O = 728.25) 476 m/z =742.83 477 m/z = 742.83 (C52H30N4O2 = 742.23) (C52H30N4O2 = 742.23) 479m/z = 732.86 481 m/z = 868.01 (C50H28N4OS = 732.19) (C62H37N5O = 867.30)482 m/z = 717.83 485 m/z = 742.83 (C50H31N5O = 717.25) (C52H30N4O2 =742.23) 488 m/z = 758.89 489 m/z = 817.95 (C52H30N4OS = 758.21)(C58H35N5O = 817.28) 490 m/z = 818.98 493 m/z = 602.69 (C59H38N4O =818.30) (C43H26N2O2 = 602.19) 494 m/z = 618.75 495 m/z = 660.77(C43H26N2OS = 618.17) (C49H28N2O = 660.22) 500 m/z = 663.77 504 m/z =697.77 (C49H29NO2 = 663.22) (C49H32NO2P = 697.21) 505 m/z = 762.91 506m/z = 735.88 (C57H34N2O = 762.26) (C56H33NO = 735.25) 509 m/z = 727.86512 m/z = 727.86 (C53H33N3O = 727.26) (C53H33N3O = 727.26) 513 m/z =665.75 516 m/z = 681.81 (C47H27N3O2 = 556.21) (C47H27N3OS = 681.18) 517m/z = 681.81 518 m/z = 740.86 (C47H27N3OS = 681.18) (C53H32N4O = 740.25)519 m/z = 691.83 520 m/z = 664.76 (C50H33N3O = 691.26) (C47H26N4O =664.22) 522 m/z = 841.97 524 m/z = 757.91 (C61H35N3O2 = 841.27)(C53H31N3OS = 757.21) 525 m/z = 757.91 527 m/z = 767.93 (C53H31N3OS =757.21) (C56H37N3O = 767.29) 528 m/z = 740.86 531 m/z = 727.86(C53H32N4O = 740.25) (C53H33N3O = 727.26) 532 m/z = 727.86 533 m/z =803.96 (C53H33N3O = 727.26) (C59H37N3O = 803.29) 535 m/z = 727.86 536m/z = 664.76 (C53H33N3O = 727.26) (C47H28N4O = 664.22) 539 m/z = 665.75542 m/z = 640.86 (C47H27N3O2 = 665.21) (C53H32N4O = 740.25) 543 m/z =691.83 544 m/z = 741.85 (C50H33N3O = 691.26) (C53H31N3O2 = 741.24) 547m/z = 757.91 548 m/z = 807.97 (C53H31N3OS = 757.21) (C57H33N3OS =807.23) 549 m/z = 816.96 550 m/z = 767.93 (C59H36N4O = 816.28)(C56H37N3O = 767.29) 554 m/z = 665.75 555 m/z = 728.85 (C46H26N4O =652.22) (C52H32N4O = 728.25) 557 m/z = 728.85 558 m/z = 804.95(C52H32N4O = 728.25) (C58H36N4O = 804.28) 564 m/z = 741.85 565 m/z =692.82 (C52H31N5O = 741.25) (C49H32N4O = 692.26) 566 m/z = 665.75 569m/z = 742.84 (C46H27N5O = 665.22) (C52H30N4O2 = 742.24) 573 m/z = 768.92574 m/z = 741.85 (C55H36N4O = 768.29) (C52H31N5O = 741.25) 580 m/z =521.62 564 m/z = 741.85 (C39H23NO = 521.18) (C52H31N5O = 741.25) 565 m/z= 692.82 566 m/z = 665.76 (C49H32N4O=692.26) (C46H27N5O=665.22) 569 m/z= 742.84 573 m/z = 768.92 (C52H30N4O2 = 742.24) (C55H36N4O = 768.29) 574m/z = 741.85 580 m/z = 521.62 (C52H31N5O = 741.25) (C39H23NO = 521.18)583 m/z = 834.01 584 m/z = 894.05 (C59H35N3OS = 833.25) (C65H39N3O2 =893.30) 585 m/z = 599.69 587 m/z = 675.79 (C43H25N3O = 599.20)(C49H29N3O = 675.23) 588 m/z = 725.85 594 m/z = 662.79 (C53H31N3O =725.25) (C49H30N2O = 662.24) 597 m/z = 652.76 598 m/z = 652.76(C46H28N4O = 652.23) (C46H28N4O = 652.23) 599 m/z = 728.86 600 m/z =728.86 (C52H32N4O = 728.26) (C52H32N4O = 728.26) 601 m/z = 666.74 605m/z = 758.90 (C46H26H4O2 = 666.21) (C52H30N4OS = 758.21) 606 m/z =741.85 611 m/z = 727.87 (C52H31N5O = 741.25) (C53H33N3O = 727.26) 612m/z = 664.77 615 m/z = 740.87 (C47H28N4O = 664.23) (C53H32N4O = 740.26)618 m/z = 767.93 620 m/z = 642.78 (C56H37N3O = 767.29) (C44H26N4S =642.19) 623 m/z = 668.82 624 m/z = 794.98 (C46H28N4S = 668.20)(C56H34N4S = 794.25) 626 m/z = 821.01 629 m/z = 682.80 (C56H36N4S =820.27) (C46H26N4OS = 682.18) 632 m/z = 698.86 634 m/z = 708.88(C46H26N4S2 = 698.16) (C49H32N4S = 708.23) 635 m/z = 681.82 636 m/z =758.90 (C46H27N5S = 681.20) (C52H30N4OS = 758.21) 640 m/z = 774.96 641m/z = 834.01 (C52H30N4S2 = 774.19) (C58H35N5S = 833.26) 644 m/z = 587.74646 m/z = 613.78 (C43H25NS = 587.17) (C45H27NS = 613.19) 649 m/z =537.68 651 m/z = 715.91 (C39H23NS = 537.16) (C53H33NS = 715.23) 652 m/z= 669.86 653 m/z = 911.10 (C47H27NS2 = 669.16) (C64H38N4OS = 910.28) 654m/z = 834.01 655 m/z = 768.98 (C59H35N3OS = 833.25) (C56H36N2S = 768.26)657 m/z = 539.66 659 m/z = 741.91 (C37H21N3S = 539.15) (C53H31N3S =741.22) 660 m/z = 668.82 661 m/z = 677.87 (C46H28N4S = 668.20) (C50H31NS= 677.22) 664 m/z = 652.82 665 m/z = 678.85 (C47H28N2S = 652.20)(C49H30N2S = 678.21) 666 m/z = 675.85 670 m/z = 676.84 (C50H29NS =675.2) (C49H28N2S = 676.20) 672 m/z = 891.00 674 m/z = 668.82 (C58H34N4S= 818.25) (C46H28N4S = 668.2) 675 m/z = 744.92 677 m/z = 744.92(C52H32N4S = 744.23) (C52H32N4S = 744.23) 680 m/z = 758.90 682 m/z =758.90 (C52H30N4OS = 758.21) (C52H30N4OS = 758.21) 683 m/z = 849.04 685m/z = 884.07 (C58H32N4S2 = 848.21) (C62H37N5S = 883.28) 687 m/z = 706.83688 m/z = 758.90 (C47H26N6S = 706.19) (C52H30N4OS = 758.21) 691 m/z =774.96 692 m/z = 875.08 (C52H30N4S2 = 774.19) (C60H34N4S2 = 874.22) 695m/z = 757.91 696 m/z = 644.84 (C52H31N5S = 757.23) (C46H32H2S = 644.23)697 m/z = 618.75 700 m/z = 768.94 (C43H26N2OS = 618.18) (C54H32N4S =768.23) 703 m/z = 743.94 704 m/z = 834.01 (C53H29NS2 = 743.17)(C59H35N3OS = 833.25) 707 m/z = 691.85 708 m/z = 668.82 (C49H29N3S =691.21) (C46H28N4S = 668.20) 709 m/z = 713.83 713 m/z = 667.83(C49H32NOPS = 713.19) (C47H29N3S = 667.21) 714 m/z = 743.93 716 m/z =743.93 (C53H33N3S = 743.24) (C53H33N3S = 743.24) 717 m/z = 820.03 721m/z = 793.99 (C59H37N3S = 819.27) (C57H35N3S = 793.26) 728 m/z = 808.01729 m/z = 680.83 (C58H37N3S = 807.27) (C47H28N4S = 680.20) 731 m/z =757.91 732 m/z = 757.91 (C53H31N3OS = 757.22) (C53H31N3OS = 757.22) 733m/z = 824.03 734 m/z = 824.03 (C57H33N3S2 = 823.21) (C57H33N3S2 =823.21) 735 m/z = 833.03 736 m/z = 783.99 (C59H36N4S = 832.27)(C56H37N3S = 783.27) 741 m/z = 820.03 743 m/z = 793.99 (C59H37N3S =819.27) (C57H35N3S = 793.26) 745 m/z = 743.93 748 m/z = 665.75(C53H33N3S = 743.24) (C47H27N3O2 = 664.21) 750 m/z = 747.93 752 m/z =707.89 (C51H29N3S2 = 747.18) (C50H33N3S = 707.24) 756 m/z = 757.91 757m/z = 824.03 (C53H31N3OS = 757.22) (C57H33N3S2 = 823.21) 761 m/z =756.93 764 m/z = 768.94 (C53H32N4S = 756.23) (C54H32N4S = 768.23) 766m/z = 793.99 767 m/z = 591.73 (C57H35N3S = 793.26) (C41H25N3S = 591.18)769 m/z = 718.88 771 m/z = 668.82 (C50H30N4S = 718.22) (C46H28N4S =668.20) 773 m/z = 744.92 775 m/z = 845.04 (C52H32N4S = 744.23)(C60H36N4S = 844.27) 779 m/z = 782.92 783 m/z = 698.86 (C54H30N4OS =782.21) (C46H26N4S2 = 698.16) 784 m/z = 757.91 786 m/z = 781.94(C52H31N5S = 757.23) (C54H31N5S = 781.23) 787 m/z = 758.90 789 m/z =758.90 (C52H30N4OS = 758.21) (C52H30N4OS = 758.21) 791 m/z = 774.96 792m/z = 834.01 (C52H30N4S2 = 774.19) (C58H35N5S = 833.26) 793 m/z = 885.10798 m/z = 589.76 (C63H40N4S = 884.30) (C43H27NS = 589.19) 801 m/z =644.84 802 m/z = 537.68 (C46H32N2S = 644.23) (C39H23NS = 537.16) 807 m/z= 758.90 809 m/z = 615.75 (C52H30N4OS = 758.21) (C43H25N3S = 615.18) 810m/z = 539.66 814 m/z = 675.85 (C37H21N3S = 539.15) (C50H29NS = 675.20)816 m/z = 641.79 817 m/z = 565.69 (C4527N3S = 641.19) (C39H23N3S =565.16) 818 m/z = 602.75 822 m/z = 845.04 (C43H26N2S = 602.18)(C60H36N4S = 844.27) 823 m/z = 847.05 825 m/z = 742.90 (C60H38N4S =846.28) (C52H30N4S = 742.22) 829 m/z = 744.92 831 m/z = 821.01(C52H32N4S = 744.23) (C58H36N4S = 820.27) 833 m/z = 758.90 836 m/z =748.92 (C52H30N4OS = 758.21) (C50H28N4S2 = 748.18) 838 m/z = 884.07 842m/z = 758.90 (C62H37N5S = 883.28) (C52H30N4OS = 758.21) 844 m/z = 774.96847 m/z = 784.98 (C52H304S2 = 774.19) (C55H36N4S = 784.27) 848 m/z =757.91 849 m/z = 644.84 (C52H31N5S = 757.23) (C46H32N2S = 644.23) 858m/z = 835.00 860 m/z = 691.85 (C58H34N4OS = 834.25) (C49H29N3S = 691.21)861 m/z = 668.82 862 m/z = 713.83 (C46H28N4S = 668.20) (C49H32OPS =713.19) 863 m/z = 678.85 870 m/z = 667.83 (C49H30N2S = 679.21)(C47H29N3S = 667.21) 871 m/z = 743.93 872 m/z = 820.03 (C53H33N3S =743.24) (C59H37N3S = 819.27) 883 m/z = 757.91 884 m/z = 757.91(C53H31N3OS = 757.22) (C53H31N3OS = 757.22) 887 m/z = 833.03 888 m/z =783.99 (C59H36N4S = 832.27) (C56H37N3S = 783.27) 890 m/z = 591.73 893m/z = 820.03 (C41H25N3S = 591.18) (C59H37N3S = 819.27) 905 m/z = 757.91908 m/z = 773.97 (C53H31N3OS = 757.22) (C53H31N3S2 = 773.20) 910 m/z =783.99 911 m/z = 756.93 (C56H37N3S = 783.27) (C53H32N4S = 756.23) 916m/z = 744.92 918 m/z = 821.01 (C52H32N4S = 744.23) (C58H36N4S = 820.27)919 m/z = 682.80 920 m/z = 682.80 (C46H26N4OS = 682.18) (C46H26N4OS =682.18) 923 m/z = 698.86 924 m/z = 757.91 (C46H26N4S2 = 698.16)(C52H31N5S = 757.23) 930 m/z = 774.96 931 m/z = 774.96 (C52H30N4S2 =774.19) (C52H30N4S2 = 774.19) 932 m/z = 834.01 943 m/z = 834.01(C58H35N5S = 833.26) (C59H35N3OS = 833.25) 945 m/z = 539.66 952 m/z =564.71 (C37H21N3S = 539.15) (C40H24N2S = 563.17) 956 m/z = 678.85 957m/z = 675.85 (C49H30N2S = 678.21) (C50H29NS = 675.20) 960 m/z = 600.74963 m/z = 768.94 (C43H24N2S = 600.17) (C54H32N4S = 768.23) 965 m/z =668.82 968 m/z = 821.01 (C46H28N4S = 668.20) (C58H36N4S = 820.27) 971m/z = 758.90 979 m/z = 758.90 (C52H30N4OS = 758.21) (C52H30N4OS =758.21) 980 m/z = 758.90 984 m/z = 834.01 (C52H30N4OS = 758.21)(C58H35H5S = 833.26) 986 m/z = 757.91 991 m/z = 613.78 (C52H31N5S =757.23) (C45H27NS = 613.19) 998 m/z = 668.82 995 m/z = 834.01 (C46H28N4S= 668.20) (C59H35N3OS = 833.25) 1000 m/z = 678.85 1004 m/z = 743.93(C49H30N2S = 678.21) (C53H33N3S = 743.24) 1006 m/z = 667.83 1011 m/z =681.81 (C47H29N3S = 667.21) (C47H27N3SO = 681.19) 1015 m/z = 707.89 1080m/z = 835.00 (C50H33N3S = 707.24) (C58H34N4OS = 834.25) 1086 m/z =691.85 1098 m/z = 676.64 (C49H29N3S = 691.21) (C49H28N2S = 676.20) 1099m/z = 692.84 (C48H26N4S = 692.20)

<Experimental Example 1> Manufacture of Organic Light Emitting DeviceComparative Example 1

1) Manufacture of Organic Light Emitting Device

A transparent indium tin oxide (ITO) electrode thin film obtained fromglass for an OLED (manufactured by Samsung-Corning Co., Ltd.) wasultrasonic cleaned using trichloroethylene, acetone, ethanol anddistilled water consecutively for 5 minutes each, stored in isopropanol,and used.

Next, an ITO substrate was installed in a substrate folder of a vacuumdeposition apparatus, and the following4,4′,4″-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) wasintroduced to a cell in the vacuum deposition apparatus.

Subsequently, the chamber was evacuated until the degree of vacuumtherein reached 10⁻⁶ torr, and then 2-TNATA was evaporated by applying acurrent to the cell to deposit a hole injection layer having a thicknessof 600 Å on the ITO substrate.

To another cell of the vacuum deposition apparatus, the followingN,N′-bis(α-naphthyl)-N,N′-diphenyl-4,4′-diamine (NPB) was introduced,and evaporated by applying a current to the cell to deposit a holetransfer layer having a thickness of 300 Å on the hole injection layer.

After forming the hole injection layer and the hole transfer layer asabove, a blue light emitting material having a structure as below wasdeposited thereon as a light emitting layer. Specifically, in one sidecell in the vacuum deposition apparatus, H1, a blue light emitting hostmaterial, was vacuum deposited to a thickness of 200 Å, and D1, a bluelight emitting dopant material, was vacuum deposited thereon by 5% withrespect to the host material.

Subsequently, a compound of the following Structural Formula E1 wasdeposited to a thickness of 300 Å as an electron transfer layer.

As an electron injection layer, lithium fluoride (LiF) was deposited toa thickness of 10 Å, and an Al cathode was employed to a thickness of1,000 Å, and as a result, an OLED was manufactured.

Meanwhile, all the organic compounds required to manufacture the OLEDwere vacuum sublimation purified under 10⁻⁸ torr to 10⁻⁶ torr by eachmaterial to be used in the OLED manufacture.

Comparative Example 2 to Comparative Example 5

Organic electroluminescent devices were manufactured in the same manneras in Comparative Example 1 except that Compound A, Compound B, CompoundC and Compound D were used instead of E1 used when forming the electrontransfer layer.

Example 1 to Example 469

Organic electroluminescent devices were manufactured in the same manneras in Comparative Example 1 except that compounds listed in thefollowing Table 20 were used instead of E1 used when forming theelectron transfer layer.

Results of measuring driving voltage, light emission efficiency, colorcoordinate (CIE) and lifetime of each of the blue organic light emittingdevices manufactured according to the present disclosure are as shown inthe following Table 20.

TABLE 20 Light Driving Emission Voltage Efficiency CIE Lifetime Compound(V) (cd/A) (x, y) (T95) Comparative E1 5.21 4.11 (0.134, 24 Example 10.100) Comparative A 4.13 3.20 (0.134, 13 Example 2 0.104) Comparative B4.11 3.12 (0.134, 10 Example 3 0.104) Comparative C 5.67 5.11 (0.134, 21Example 4 0.104) Comparative D 5.67 5.12 (0.134, 20 Example 5 0.104)Example 1 1 5.44 6.47 (0.134, 36 0.102) Example 2 4 4.47 6.87 (0.134, 400.100) Example 3 5 4.67 6.64 (0.129, 38 0.100) Example 4 7 4.82 6.55(0.130, 36 0.099) Example 5 8 4.44 6.97 (0.134, 40 0.101) Example 6 94.61 6.89 (0.134, 40 0.103) Example 7 11 5.35 6.30 (0.134, 33 0.102)Example 8 12 5.62 5.95 (0.134, 42 0.103) Example 9 13 5.40 6.12 (0.134,39 0.101) Example 10 15 5.50 5.89 (0.134, 41 0.100) Example 11 16 5.446.01 (0.134, 36 0.101) Example 12 17 5.34 6.58 (0.134, 45 0.100) Example13 18 5.38 6.93 (0.134, 43 0.100) Example 14 24 4.91 6.32 (0.134, 410.100) Example 15 25 4.98 6.44 (0.134, 40 0.100) Example 16 28 5.62 6.38(0.134, 35 0.100) Example 17 30 5.66 6.04 (0.131, 30 0.102) Example 1835 5.40 6.49 (0.134, 31 0.101) Example 19 36 5.60 6.22 (0.129, 29 0.100)Example 20 37 4.70 6.01 (0.134, 36 0.101) Example 21 38 5.40 6.12(0.134, 44 0.103) Example 22 41 5.60 6.21 (0.134, 43 0.102) Example 2342 5.45 6.22 (0.134, 37 0.101) Example 24 44 5.39 5.95 (0.134, 33 0.102)Example 25 45 4.96 5.95 (0.134, 42 0.101) Example 26 47 4.91 6.13(0.134, 39 0.101) Example 27 52 4.91 5.85 (0.134, 41 0.100) Example 2853 4.98 6.38 (0.134, 42 0.101) Example 29 56 4.91 5.85 (0.134, 41 0.100)Example 30 57 4.98 6.38 (0.134, 42 0.101) Example 31 58 5.44 6.47(0.134, 36 0.102) Example 32 64 4.47 6.87 (0.134, 40 0.100) Example 3368 4.67 6.64 (0.129, 38 0.100) Example 34 69 4.82 6.55 (0.130, 36 0.099)Example 35 70 4.44 6.97 (0.134, 40 0.101) Example 36 72 4.61 6.89(0.134, 40 0.103) Example 37 75 5.35 6.30 (0.134, 33 0.102) Example 3877 5.62 5.95 (0.134, 42 0.103) Example 39 79 5.40 6.12 (0.134, 39 0.101)Example 40 80 5.50 5.89 (0.134, 41 0.100) Example 41 84 5.44 6.01(0.134, 36 0.101) Example 42 86 5.34 6.58 (0.134, 45 0.100) Example 4388 5.38 6.93 (0.134, 43 0.100) Example 44 89 4.91 6.32 (0.134, 41 0.100)Example 45 91 4.98 6.44 (0.134, 40 0.100) Example 46 92 5.62 6.38(0.134, 35 0.100) Example 47 97 5.66 6.04 (0.131, 30 0.102) Example 48100 5.40 6.49 (0.134, 31 0.101) Example 49 102 5.60 6.22 (0.129, 290.100) Example 50 103 4.70 6.01 (0.134, 36 0.101) Example 51 107 5.406.12 (0.134, 44 0.103) Example 52 112 5.60 6.21 (0.134, 43 0.102)Example 53 113 5.45 6.22 (0.134, 37 0.101) Example 54 114 5.39 5.95(0.134, 33 0.102) Example 55 116 4.96 5.95 (0.134, 42 0.101) Example 56119 5.44 6.47 (0.134, 36 0.102) Example 57 120 4.47 6.87 (0.134, 400.100) Example 58 121 4.67 6.64 (0.129, 38 0.100) Example 59 128 4.826.55 (0.130, 36 0.099) Example 60 132 4.44 6.97 (0.134, 40 0.101)Example 61 133 4.61 6.89 (0.134, 40 0.103) Example 62 135 5.35 6.30(0.134, 33 0.102) Example 63 139 5.62 5.95 (0.134, 42 0.103) Example 64140 5.40 6.12 (0.134, 39 0.101) Example 65 141 5.50 5.89 (0.134, 410.100) Example 66 142 5.44 6.01 (0.134, 36 0.101) Example 67 145 5.346.58 (0.134, 45 0.100) Example 68 149 5.44 6.47 (0.134, 36 0.102)Example 69 156 4.47 6.87 (0.134, 40 0.100) Example 70 157 4.67 6.64(0.129, 38 0.100) Example 71 159 4.82 6.55 (0.130, 36 0.099) Example 72161 4.44 6.97 (0.134, 40 0.101) Example 73 165 4.61 6.89 (0.134, 400.103) Example 74 166 5.35 6.30 (0.134, 33 0.102) Example 75 168 5.625.95 (0.134, 42 0.103) Example 76 170 5.40 6.12 (0.134, 39 0.101)Example 77 171 5.50 5.89 (0.134, 41 0.100) Example 78 172 5.44 6.01(0.134, 36 0.101) Example 79 173 5.34 6.58 (0.134, 45 0.100) Example 80176 5.38 6.93 (0.134, 43 0.100) Example 81 178 4.91 6.32 (0.134, 410.100) Example 82 179 4.98 6.44 (0.134, 40 0.100) Example 83 180 5.626.38 (0.134, 35 0.100) Example 84 185 5.66 6.04 (0.131, 30 0.102)Example 85 187 5.40 6.49 (0.134, 31 0.101) Example 86 190 5.60 6.22(0.129, 29 0.100) Example 87 191 4.70 6.01 (0.134, 36 0.101) Example 88192 5.40 6.12 (0.134, 44 0.103) Example 89 194 5.60 6.21 (0.134, 430.102) Example 90 195 5.45 6.22 (0.134, 37 0.101) Example 91 196 5.395.95 (0.134, 33 0.102) Example 92 200 4.96 5.95 (0.134, 42 0.101)Example 93 202 4.91 6.13 (0.134, 39 0.101) Example 94 204 4.91 5.85(0.134, 41 0.100) Example 95 207 4.98 6.38 (0.134, 42 0.101) Example 96210 4.74 6.75 (0.134, 51 0.101) Example 97 213 4.81 6.82 (0.134, 530.102) Example 98 214 5.16 6.20 (0.134, 38 0.101) Example 99 216 5.156.42 (0.134, 39 0.102) Example 100 217 5.31 6.30 (0.134, 37 0.103)Example 101 220 4.82 6.35 (0.134, 50 0.100) Example 102 222 4.91 6.12(0.134, 42 0.101) Example 103 223 4.98 6.51 (0.134, 39 0.101) Example104 224 5.62 6.21 (0.134, 41 0.100) Example 105 225 5.39 5.95 (0.134, 340.101) Example 106 227 4.96 6.88 (0.134, 45 0.100) Example 107 228 4.916.93 (0.134, 43 0.102) Example 108 229 4.76 6.95 (0.134, 50 0.102)Example 109 233 4.77 6.90 (0.134, 51 0.102) Example 110 237 4.98 6.05(0.134, 34 0.101) Example 111 240 5.22 6.03 (0.134, 43 0.101) Example112 243 4.82 6.84 (0.134, 52 0.101) Example 113 245 4.84 6.97 (0.134, 510.102) Example 114 247 5.38 6.88 (0.134, 41 0.100) Example 115 249 5.606.93 (0.134, 32 0.101) Example 116 251 5.45 6.95 (0.134, 45 0.100)Example 117 256 4.91 6.93 (0.134, 43 0.100) Example 118 257 4.91 6.95(0.134, 41 0.100) Example 119 259 4.98 6.23 (0.134, 40 0.100) Example120 260 5.62 5.98 (0.134, 36 0.100) Example 121 262 4.72 6.51 (0.134, 480.102) Example 122 265 4.91 6.93 (0.134, 43 0.100) Example 123 266 4.916.95 (0.134, 41 0.100) Example 124 267 4.98 6.26 (0.134, 40 0.100)Example 125 269 5.62 5.98 (0.134, 33 0.100) Example 126 271 4.91 6.32(0.134, 41 0.100) Example 127 272 4.98 6.44 (0.134, 40 0.100) Example128 273 5.62 6.38 (0.134, 35 0.100) Example 129 274 5.44 6.34 (0.134, 360.102) Example 130 276 5.62 6.20 (0.134, 39 0.101) Example 131 277 5.626.22 (0.134, 47 0.100) Example 132 279 5.62 5.98 (0.134, 33 0.100)Example 133 281 4.72 6.55 (0.134, 48 0.102) Example 134 284 4.72 6.20(0.134, 43 0.102) Example 135 285 5.40 6.12 (0.134, 39 0.101) Example136 287 5.44 6.21 (0.134, 41 0.100) Example 137 288 5.39 6.20 (0.134, 360.101) Example 138 292 4.96 6.88 (0.134, 45 0.100) Example 139 294 4.916.93 (0.134, 43 0.100) Example 140 296 4.96 6.88 (0.134, 45 0.100)Example 141 299 4.91 6.93 (0.134, 43 0.102) Example 142 302 4.98 6.22(0.134, 40 0.100) Example 143 304 4.72 6.53 (0.134, 48 0.102) Example144 305 4.74 6.75 (0.134, 51 0.101) Example 145 307 4.81 6.82 (0.134, 530.102) Example 146 308 5.16 6.20 (0.134, 38 0.101) Example 147 309 5.156.42 (0.134, 39 0.102) Example 148 310 4.74 6.75 (0.134, 51 0.101)Example 149 312 4.81 6.82 (0.134, 53 0.102) Example 150 313 5.16 6.20(0.134, 38 0.101) Example 151 315 5.15 6.42 (0.134, 39 0.102) Example152 316 5.31 6.30 (0.134, 37 0.103) Example 153 318 4.82 6.35 (0.134, 500.100) Example 154 319 4.91 6.12 (0.134, 42 0.101) Example 155 322 4.986.51 (0.134, 39 0.101) Example 156 325 5.62 6.21 (0.134, 41 0.100)Example 157 326 5.39 5.95 (0.134, 34 0.101) Example 158 327 4.96 6.88(0.134, 45 0.100) Example 159 329 4.91 6.93 (0.134, 43 0.102) Example160 331 4.76 6.95 (0.134, 50 0.102) Example 161 332 4.77 6.90 (0.134, 510.102) Example 162 336 4.98 6.05 (0.134, 34 0.101) Example 163 337 5.226.03 (0.134, 43 0.101) Example 164 338 4.82 6.84 (0.134, 52 0.101)Example 165 339 4.84 6.97 (0.134, 51 0.102) Example 166 342 5.38 6.88(0.134, 41 0.100) Example 167 343 5.60 6.93 (0.134, 32 0.101) Example168 345 5.45 6.95 (0.134, 45 0.100) Example 169 348 4.91 6.93 (0.134, 430.100) Example 170 350 4.91 6.95 (0.134, 41 0.100) Example 171 353 4.986.23 (0.134, 40 0.100) Example 172 355 5.62 5.98 (0.134, 36 0.100)Example 173 358 4.72 6.51 (0.134, 48 0.102) Example 174 359 4.91 6.93(0.134, 43 0.100) Example 175 360 4.91 6.95 (0.134, 41 0.100) Example176 364 4.98 6.26 (0.134, 40 0.100) Example 177 365 5.62 5.98 (0.134, 330.100) Example 178 367 4.91 6.32 (0.134, 41 0.100) Example 179 368 4.986.44 (0.134, 40 0.100) Example 180 373 5.62 6.38 (0.134, 35 0.100)Example 181 374 5.44 6.34 (0.134, 36 0.102) Example 182 377 5.62 6.20(0.134, 39 0.101) Example 183 378 5.62 6.22 (0.134, 47 0.100) Example184 379 5.62 5.98 (0.134, 33 0.100) Example 185 380 4.72 6.55 (0.134, 480.102) Example 186 384 4.72 6.20 (0.134, 43 0.102) Example 187 386 5.406.12 (0.134, 39 0.101) Example 188 387 5.44 6.21 (0.134, 41 0.100)Example 189 388 5.39 6.20 (0.134, 36 0.101) Example 190 392 4.96 6.88(0.134, 45 0.100) Example 191 395 4.91 6.93 (0.134, 43 0.100) Example192 396 4.96 6.88 (0.134, 45 0.100) Example 193 397 4.91 6.93 (0.134, 430.102) Example 194 399 4.98 6.22 (0.134, 40 0.100) Example 195 400 4.726.53 (0.134, 48 0.102) Example 196 401 4.72 6.53 (0.134, 48 0.102)Example 197 404 5.45 6.95 (0.134, 45 0.100) Example 198 407 4.91 6.93(0.134, 43 0.100) Example 199 408 4.91 6.95 (0.134, 41 0.100) Example200 409 4.98 6.23 (0.134, 40 0.100) Example 201 411 5.62 5.98 (0.134, 360.100) Example 202 413 4.72 6.51 (0.134, 48 0.102) Example 203 415 4.916.93 (0.134, 43 0.100) Example 204 416 4.91 6.95 (0.134, 41 0.100)Example 205 417 4.98 6.26 (0.134, 40 0.100) Example 206 421 5.62 5.98(0.134, 33 0.100) Example 207 423 4.91 6.32 (0.134, 41 0.100) Example208 424 4.98 6.44 (0.134, 40 0.100) Example 209 426 4.91 6.95 (0.134, 410.100) Example 210 431 4.98 6.23 (0.134, 40 0.100) Example 211 432 5.625.98 (0.134, 36 0.100) Example 212 433 4.72 6.51 (0.134, 48 0.102)Example 213 436 4.91 6.93 (0.134, 43 0.100) Example 214 438 4.91 6.95(0.134, 41 0.100) Example 215 440 4.98 6.26 (0.134, 40 0.100) Example216 441 5.62 5.98 (0.134, 33 0.100) Example 217 443 4.91 6.32 (0.134, 410.100) Example 218 447 4.98 6.44 (0.134, 40 0.100) Example 219 448 5.626.38 (0.134, 35 0.100) Example 220 449 5.44 6.34 (0.134, 36 0.102)Example 221 450 5.62 6.20 (0.134, 39 0.101) Example 222 452 5.62 6.22(0.134, 47 0.100) Example 223 456 5.62 5.98 (0.134, 33 0.100) Example224 460 4.72 6.55 (0.134, 48 0.102) Example 225 462 4.72 6.20 (0.134, 430.102) Example 226 465 5.40 6.12 (0.134, 39 0.101) Example 227 467 5.446.21 (0.134, 41 0.100) Example 228 468 5.39 6.20 (0.134, 36 0.101)Example 229 470 4.96 6.88 (0.134, 45 0.100) Example 230 475 4.91 6.93(0.134, 43 0.100) Example 231 476 4.96 6.88 (0.134, 45 0.100) Example232 477 4.91 6.93 (0.134, 43 0.102) Example 233 479 4.98 6.22 (0.134, 400.100) Example 234 481 4.72 6.53 (0.134, 48 0.102) Example 235 482 4.726.53 (0.134, 48 0.102) Example 236 485 5.45 6.95 (0.134, 45 0.100)Example 237 488 4.91 6.93 (0.134, 43 0.100) Example 238 489 4.91 6.95(0.134, 41 0.100) Example 239 490 4.98 6.23 (0.134, 40 0.100) Example240 493 4.74 6.75 (0.134, 51 0.101) Example 241 494 4.81 6.82 (0.134, 530.102) Example 242 495 5.16 6.20 (0.134, 38 0.101) Example 243 500 5.156.42 (0.134, 39 0.102) Example 244 504 5.31 6.30 (0.134, 37 0.103)Example 245 505 4.82 6.35 (0.134, 50 0.100) Example 246 506 4.91 6.12(0.134, 42 0.101) Example 247 509 4.98 6.51 (0.134, 39 0.101) Example248 512 5.62 6.21 (0.134, 41 0.100) Example 249 513 5.39 5.95 (0.134, 340.101) Example 250 516 4.96 6.88 (0.134, 45 0.100) Example 251 517 4.916.93 (0.134, 43 0.102) Example 252 518 4.76 6.95 (0.134, 50 0.102)Example 253 519 4.77 6.90 (0.134, 51 0.102) Example 254 520 4.98 6.05(0.134, 34 0.101) Example 255 522 5.22 6.03 (0.134, 43 0.101) Example256 524 4.82 6.84 (0.134, 52 0.101) Example 257 525 4.84 6.97 (0.134, 510.102) Example 258 527 5.38 6.88 (0.134, 41 0.100) Example 259 528 5.606.93 (0.134, 32 0.101) Example 260 531 5.45 6.95 (0.134, 45 0.100)Example 261 532 4.91 6.93 (0.134, 43 0.100) Example 262 533 4.91 6.95(0.134, 41 0.100) Example 263 535 4.98 6.23 (0.134, 40 0.100) Example264 536 5.62 5.98 (0.134, 36 0.100) Example 265 539 4.72 6.51 (0.134, 480.102) Example 266 542 4.91 6.93 (0.134, 43 0.100) Example 267 543 4.916.95 (0.134, 41 0.100) Example 268 544 4.98 6.26 (0.134, 40 0.100)Example 269 547 5.62 5.98 (0.134, 33 0.100) Example 270 548 4.91 6.32(0.134, 41 0.100) Example 271 549 4.98 6.44 (0.134, 40 0.100) Example272 550 5.62 6.38 (0.134, 35 0.100) Example 273 554 5.44 6.34 (0.134, 360.102) Example 274 555 5.62 6.20 (0.134, 39 0.101) Example 275 557 5.626.22 (0.134, 47 0.100) Example 276 558 5.62 5.98 (0.134, 33 0.100)Example 277 564 4.72 6.55 (0.134, 48 0.102) Example 278 564 4.72 6.20(0.134, 43 0.102) Example 279 565 5.40 6.12 (0.134, 39 0.101) Example280 565 5.44 6.21 (0.134, 41 0.100) Example 281 566 5.39 6.20 (0.134, 360.101) Example 282 566 4.96 6.88 (0.134, 45 0.100) Example 283 569 4.916.93 (0.134, 43 0.100) Example 284 569 4.96 6.88 (0.134, 45 0.100)Example 285 573 4.91 6.93 (0.134, 43 0.102) Example 286 573 4.98 6.22(0.134, 40 0.100) Example 287 574 4.72 6.53 (0.134, 48 0.102) Example288 574 4.74 6.75 (0.134, 51 0.101) Example 289 580 4.81 6.82 (0.134, 530.102) Example 290 580 5.16 6.20 (0.134, 38 0.101) Example 291 583 5.156.42 (0.134, 39 0.102) Example 292 584 4.74 6.75 (0.134, 51 0.101)Example 293 585 4.81 6.82 (0.134, 53 0.102) Example 294 587 5.16 6.20(0.134, 38 0.101) Example 295 588 5.15 6.42 (0.134, 39 0.102) Example296 594 5.31 6.30 (0.134, 37 0.103) Example 297 597 4.82 6.35 (0.134, 500.100) Example 298 598 4.91 6.12 (0.134, 42 0.101) Example 299 599 4.986.51 (0.134, 39 0.101) Example 300 600 5.62 6.21 (0.134, 41 0.100)Example 301 601 5.39 5.95 (0.134, 34 0.101) Example 302 605 4.96 6.88(0.134, 45 0.100) Example 303 606 4.91 6.93 (0.134, 43 0.102) Example304 611 4.76 6.95 (0.134, 50 0.102) Example 305 612 4.77 6.90 (0.134, 510.102) Example 306 615 4.98 6.05 (0.134, 34 0.101) Example 307 618 5.226.03 (0.134, 43 0.101) Example 308 620 4.82 6.84 (0.134, 52 0.101)Example 309 623 4.84 6.97 (0.134, 51 0.102) Example 310 624 5.38 6.88(0.134, 41 0.100) Example 311 626 5.60 6.93 (0.134, 32 0.101) Example312 629 5.45 6.95 (0.134, 45 0.100) Example 313 632 4.91 6.93 (0.134, 430.100) Example 314 634 4.91 6.95 (0.134, 41 0.100) Example 315 635 4.986.23 (0.134, 40 0.100) Example 316 636 5.62 5.98 (0.134, 36 0.100)Example 317 640 4.72 6.51 (0.134, 48 0.102) Example 318 641 4.91 6.93(0.134, 43 0.100) Example 319 644 4.91 6.95 (0.134, 41 0.100) Example320 646 4.98 6.26 (0.134, 40 0.100) Example 321 649 5.62 5.98 (0.134, 330.100) Example 322 651 4.91 6.32 (0.134, 41 0.100) Example 323 652 4.986.44 (0.134, 40 0.100) Example 324 653 5.62 6.38 (0.134, 35 0.100)Example 325 654 5.44 6.34 (0.134, 36 0.102) Example 326 655 5.62 6.20(0.134, 39 0.101) Example 327 657 5.62 6.22 (0.134, 47 0.100) Example328 659 5.62 5.98 (0.134, 33 0.100) Example 329 660 4.72 6.55 (0.134, 480.102) Example 330 661 4.72 6.20 (0.134, 43 0.102) Example 331 664 5.406.12 (0.134, 39 0.101) Example 332 665 5.44 6.21 (0.134, 41 0.100)Example 333 666 5.39 6.20 (0.134, 36 0.101) Example 334 670 4.96 6.88(0.134, 45 0.100) Example 335 672 4.91 6.93 (0.134, 43 0.100) Example336 674 4.96 6.88 (0.134, 45 0.100) Example 337 675 4.91 6.93 (0.134, 430.102) Example 338 677 4.98 6.22 (0.134, 40 0.100) Example 339 680 4.726.53 (0.134, 48 0.102) Example 340 682 4.72 6.53 (0.134, 48 0.102)Example 341 683 5.45 6.95 (0.134, 45 0.100) Example 342 685 4.91 6.93(0.134, 43 0.100) Example 343 687 4.91 6.95 (0.134, 41 0.100) Example344 688 4.98 6.23 (0.134, 40 0.100) Example 345 691 5.62 5.98 (0.134, 360.100) Example 346 692 4.72 6.51 (0.134, 48 0.102) Example 347 695 4.916.93 (0.134, 43 0.100) Example 348 696 4.91 6.95 (0.134, 41 0.100)Example 349 697 4.98 6.26 (0.134, 40 0.100) Example 350 700 5.62 5.98(0.134, 33 0.100) Example 351 703 4.91 6.32 (0.134, 41 0.100) Example352 704 4.98 6.44 (0.134, 40 0.100) Example 353 707 4.91 6.95 (0.134, 410.100) Example 354 708 4.98 6.23 (0.134, 40 0.100) Example 355 709 5.625.98 (0.134, 36 0.100) Example 356 713 4.72 6.51 (0.134, 48 0.102)Example 357 714 4.91 6.93 (0.134, 43 0.100) Example 358 716 4.91 6.95(0.134, 41 0.100) Example 359 717 4.98 6.26 (0.134, 40 0.100) Example360 721 5.62 5.98 (0.134, 33 0.100) Example 361 728 4.91 6.32 (0.134, 410.100) Example 362 729 4.98 6.44 (0.134, 40 0.100) Example 363 731 5.626.38 (0.134, 35 0.100) Example 364 732 5.44 6.34 (0.134, 36 0.102)Example 365 733 5.62 6.20 (0.134, 39 0.101) Example 366 734 5.62 6.22(0.134, 47 0.100) Example 367 735 5.62 5.98 (0.134, 33 0.100) Example368 736 4.72 6.55 (0.134, 48 0.102) Example 369 741 4.72 6.20 (0.134, 430.102) Example 370 743 4.74 6.75 (0.134, 51 0.101) Example 371 745 4.816.82 (0.134, 53 0.102) Example 372 748 5.16 6.20 (0.134, 38 0.101)Example 373 750 5.15 6.42 (0.134, 39 0.102) Example 374 752 5.31 6.30(0.134, 37 0.103) Example 375 756 4.82 6.35 (0.134, 50 0.100) Example376 757 4.91 6.12 (0.134, 42 0.101) Example 377 761 4.98 6.51 (0.134, 390.101) Example 378 764 5.62 6.21 (0.134, 41 0.100) Example 379 766 5.395.95 (0.134, 34 0.101) Example 380 767 4.96 6.88 (0.134, 45 0.100)Example 381 769 4.91 6.93 (0.134, 43 0.102) Example 382 771 4.76 6.95(0.134, 50 0.102) Example 383 773 4.77 6.90 (0.134, 51 0.102) Example384 775 4.98 6.05 (0.134, 34 0.101) Example 385 779 5.22 6.03 (0.134, 430.101) Example 386 783 4.82 6.84 (0.134, 52 0.101) Example 387 784 4.846.97 (0.134, 51 0.102) Example 388 786 5.38 6.88 (0.134, 41 0.100)Example 389 787 5.60 6.93 (0.134, 32 0.101) Example 390 789 5.45 6.95(0.134, 45 0.100) Example 391 791 4.91 6.93 (0.134, 43 0.100) Example392 792 4.91 6.95 (0.134, 41 0.100) Example 393 793 4.98 6.23 (0.134, 400.100) Example 394 798 5.62 5.98 (0.134, 36 0.100) Example 395 801 4.726.51 (0.134, 48 0.102) Example 396 802 4.91 6.93 (0.134, 43 0.100)Example 397 807 4.91 6.95 (0.134, 41 0.100) Example 398 809 4.98 6.26(0.134, 40 0.100) Example 399 810 5.62 5.98 (0.134, 33 0.100) Example400 814 4.91 6.32 (0.134, 41 0.100) Example 401 816 4.98 6.44 (0.134, 400.100) Example 402 817 5.62 6.38 (0.134, 35 0.100) Example 403 818 5.446.34 (0.134, 36 0.102) Example 404 822 5.62 6.20 (0.134, 39 0.101)Example 405 823 5.62 6.22 (0.134, 47 0.100) Example 406 825 5.62 5.98(0.134, 33 0.100) Example 407 829 4.72 6.55 (0.134, 48 0.102) Example408 831 4.72 6.20 (0.134, 43 0.102) Example 409 833 5.40 6.12 (0.134, 390.101) Example 410 836 5.44 6.21 (0.134, 41 0.100) Example 411 838 5.396.20 (0.134, 36 0.101) Example 412 842 4.96 6.88 (0.134, 45 0.100)Example 413 844 4.91 6.93 (0.134, 43 0.100) Example 414 847 4.96 6.88(0.134, 45 0.100) Example 415 848 4.91 6.93 (0.134, 43 0.102) Example416 849 4.98 6.22 (0.134, 40 0.100) Example 417 858 4.72 6.53 (0.134, 480.102) Example 418 860 4.74 6.75 (0.134, 51 0.101) Example 419 861 4.816.82 (0.134, 53 0.102) Example 420 862 5.16 6.20 (0.134, 38 0.101)Example 421 863 5.15 6.42 (0.134, 39 0.102) Example 422 870 4.74 6.75(0.134, 51 0.101) Example 423 871 4.81 6.82 (0.134, 53 0.102) Example424 872 5.16 6.20 (0.134, 38 0.101) Example 425 883 5.15 6.42 (0.134, 390.102) Example 426 884 5.31 6.30 (0.134, 37 0.103) Example 427 887 4.826.35 (0.134, 50 0.100) Example 428 888 4.91 6.12 (0.134, 42 0.101)Example 429 890 4.98 6.51 (0.134, 39 0.101) Example 430 893 5.62 6.21(0.134, 41 0.100) Example 431 905 5.39 5.95 (0.134, 34 0.101) Example432 908 4.96 6.88 (0.134, 45 0.100) Example 433 910 4.91 6.93 (0.134, 430.102) Example 434 911 4.76 6.95 (0.134, 50 0.102) Example 435 916 4.776.90 (0.134, 51 0.102) Example 436 918 4.98 6.05 (0.134, 34 0.101)Example 437 919 5.22 6.03 (0.134, 43 0.101) Example 438 920 4.82 6.84(0.134, 52 0.101) Example 439 923 4.84 6.97 (0.134, 51 0.102) Example440 924 5.38 6.88 (0.134, 41 0.100) Example 441 930 5.60 6.93 (0.134, 320.101) Example 442 931 5.45 6.95 (0.134, 45 0.100) Example 443 932 4.916.93 (0.134, 43 0.100) Example 444 943 4.91 6.95 (0.134, 41 0.100)Example 445 945 4.98 6.23 (0.134, 40 0.100) Example 446 952 5.62 5.98(0.134, 36 0.100) Example 447 956 4.72 6.51 (0.134, 48 0.102) Example448 957 4.91 6.93 (0.134, 43 0.100) Example 449 960 4.91 6.95 (0.134, 410.100) Example 450 963 4.98 6.26 (0.134, 40 0.100) Example 451 965 5.625.98 (0.134, 33 0.100) Example 452 968 4.91 6.32 (0.134, 41 0.100)Example 453 971 4.98 6.44 (0.134, 40 0.100) Example 454 979 5.62 6.38(0.134, 35 0.100) Example 455 980 5.44 6.34 (0.134, 36 0.102) Example456 984 5.62 6.20 (0.134, 39 0.101) Example 457 986 5.62 6.22 (0.134, 470.100) Example 458 991 5.62 5.98 (0.134, 33 0.100) Example 459 995 4.726.55 (0.134, 48 0.102) Example 460 998 4.72 6.20 (0.134, 43 0.102)Example 461 1000 5.40 6.12 (0.134, 39 0.101) Example 462 1004 5.44 6.21(0.134, 41 0.100) Example 463 1006 5.39 6.20 (0.134, 36 0.101) Example464 1011 4.96 6.88 (0.134, 45 0.100) Example 465 1015 4.91 6.93 (0.134,43 0.100) Example 466 1080 4.96 6.88 (0.134, 45 0.100) Example 467 10864.91 6.93 (0.134, 43 0.102) Example 468 1098 4.98 6.22 (0.134, 40 0.100)Example 469 1099 4.72 6.53 (0.134, 48 0.102)

As seen from Table 20, the organic light emitting device using thecompound of the present disclosure as an electron transfer layermaterial of a blue organic light emitting device had lower drivingvoltage and improved light emission efficiency and lifetime compared toComparative Example 1, Comparative Example 2, Comparative Example 3 andComparative Example 4. Such results are due to the fact that thecompound is a bipolar type having both a p-type and an n-type, andtherefore, hole leakage is prevented and electrons are effectivelyinjected to a light emitting layer.

1. A heterocyclic compound represented by the following Chemical Formula1:

wherein, in Chemical Formula 1, X is O or S, L is a direct bond; asubstituted or unsubstituted C6 to C60 arylene group; or a substitutedor unsubstituted C2 to C60 heteroarylene group, Z and R1 are eachindependently a substituted or unsubstituted C1 to C60 alkyl group; asubstituted or unsubstituted C2 to C60 alkenyl group; a substituted orunsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60heterocycloalkyl group; a substituted or unsubstituted C6 to C60 arylgroup; a substituted or unsubstituted C2 to C60 heteroaryl group; asubstituted or unsubstituted C1 to C20 alkylamine group; a substitutedor unsubstituted C6 to C60 arylamine group; a substituted orunsubstituted C2 to C60 heteroarylamine group; or a substituted orunsubstituted phosphine oxide group, R2 to R7 are each independentlyhydrogen; deuterium; a halogen group; a cyano group; a substituted orunsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 arylgroup; or a substituted or unsubstituted C2 to C60 heteroaryl group, ais 1 or 2, b is an integer of 1 to 3, m and n are each an integer of 1to 5, and when a, b, m and n are each 2 or greater, substituents in theparentheses are the same as or different from each other.
 2. Theheterocyclic compound of claim 1, wherein Chemical Formula 1 isrepresented by any one of the following Chemical Formula 2 to ChemicalFormula 4:

in Chemical Formulae 2 to 4, X, L, Z, R1 to R7, a, b, m and n have thesame definitions as in Chemical Formula
 1. 3. The heterocyclic compoundof claim 1, wherein Chemical Formula 1 is represented by the followingChemical Formula 1-1:

in Chemical Formula 1-1, X, L, Z, R2 to R7, a, b, m and n have the samedefinitions as in Chemical Formula 1, L′ is a direct bond; a substitutedor unsubstituted C6 to C60 arylene group; or a substituted orunsubstituted C2 to C60 heteroarylene group, and Z′ is a substituted orunsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60heterocycloalkyl group; a substituted or unsubstituted C6 to C60 arylgroup; or a substituted or unsubstituted C2 to C60 heteroaryl group. 4.The heterocyclic compound of claim 1, wherein L is a direct bond; asubstituted or unsubstituted phenylene group; a substituted orunsubstituted biphenylene group; a substituted or unsubstitutedterphenylene group; a substituted or unsubstituted naphthylene group; asubstituted or unsubstituted anthracenylene group; a substituted orunsubstituted triphenylenylene group; a substituted or unsubstitutedphenanthrenylene group; a substituted or unsubstituted divalent pyridinegroup; a substituted or unsubstituted divalent pyrimidine group; or asubstituted or unsubstituted divalent triazine group.
 5. Theheterocyclic compound of claim 1, wherein R1 is a substituted orunsubstituted C6 to C30 aryl group.
 6. The heterocyclic compound ofclaim 1, wherein Z is a substituted or unsubstituted phenyl group; abiphenyl group; a terphenyl group; a naphthyl group; a triphenylenylgroup; a phenanthrenyl group; an anthracenyl group; a dimethylfluorenylgroup; a diphenylfluorenyl group; a spirobifluorenyl group; anisoquinolinyl group; a quinazolinyl group; a phenoxazinyl group; aphenothiazinyl group; an indolocarbazole group; a substituted orunsubstituted pyridine group; a substituted or unsubstituted pyrimidinegroup; a substituted or unsubstituted triazine group; a substituted orunsubstituted carbazole group; a substituted or unsubstitutedbenzocarbazole group; a substituted or unsubstituted phenanthrolinylgroup; a substituted or unsubstituted dibenzofuran group; a substitutedor unsubstituted dibenzothiophene group; a substituted or unsubstituteddihydroacridine group; or a substituted or unsubstituted phosphine oxidegroup.
 7. The heterocyclic compound of claim 1, wherein Chemical Formula1 is represented by any one of the following compounds:


8. An organic light emitting device comprising: a first electrode; asecond electrode; and an organic material layer provided between thefirst electrode and the second electrode, wherein the organic materiallayer includes the heterocyclic compound of claim
 1. 9. The organiclight emitting device of claim 8, wherein the organic material layerincludes an electron transfer layer, and the electron transfer layerincludes the heterocyclic compound.
 10. The organic light emittingdevice of claim 8, further comprising one, two or more layers selectedfrom the group consisting of a light emitting layer, a hole injectionlayer, a hole transfer layer, an electron injection layer, an electrontransfer layer, an electron blocking layer and a hole blocking layer.11. The organic light emitting device of claim 8 comprising: the firstelectrode; a first stack provided on the first electrode and including afirst light emitting layer; a charge generation layer provided on thefirst stack; a second stack provided on the charge generation layer andincluding a second light emitting layer; and the second electrodeprovided on the second stack.
 12. The organic light emitting device ofclaim 11, wherein the charge generation layer includes the heterocycliccompound.
 13. The organic light emitting device of claim 11, wherein thecharge generation layer is an N-type charge generation layer, and thecharge generation layer includes the heterocyclic compound.